Herbicidal Sulfonamides

ABSTRACT

This invention relates to novel herbicidally active sulfonylurea compounds substituted in the positions ortho to the sulfonylurea bridge, agriculturally suitable compositions thereof and methods of their use as preemergent or postemergent herbicides or plant growth regulants.

This application is a divisional of my copending application Ser. No. 078,154, filed July 27, 1987, now U.S. Pat. No. 4,764,204, which is a divisional of Ser. No. 841,109, filed Mar. 18, 1986, now issued as U.S. Pat. No. 4,705,556, which is a divisional of Ser. No. 628,259, filed July 12, 1984, now issued as U.S. Pat. No. 4,604,131, which is a continuation-in-part of Ser. No. 520,801, filed Aug. 5, 1983, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to novel herbicidal sulfonamide compounds with substituents in both positions ortho to the sulfonylurea bridge, suitable agricultural compositions thereof and a method for their use as preemergent or postemergent herbicides for plant growth regulants.

Herbicidal sulfonamides of the type described herein are generally referred to in the art as "sulfonylurea" herbicides.

The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. This class of herbicides, generally consists of a sulfonylurea bridge, --SO₂ NHCONH--, linking two aromatic or heteroaromatic rings. See, for example, the compounds disclosed in U.S. Pat. Nos. 4,169,719, 4,127,405, 4,120,691, 4,221,585, 4,190,432, 4,225,337, 4,371,391, 4,339,266, 4,191,553, 4,305,884, 4,214,890, 4,339,267, 4,302,241, 4,342,587, 4,310,346, 4,293,330, 4,301,286, 4,370,479, 4,370,480, 4,368,067, 4,369,320, 4,348,219, 4,348,220, 4,333,760, 4,368,069, and U.S. Pat. No. 3,323,611 as well as European patent application 79300982.0 (Publication No. 7,687, published Feb. 6, 1980).

New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of undesired vegetation to permit the growth of useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such useful crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

EPO Pub. No. 7,687, discloses herbicidal sulfonylureas bearing ortho-carboxylic acid ester groups.

EPO Pub. No. 23,141, discloses herbicidal sulfonylureas bearing ortho-sulfamoyl groups.

EPO Pub. No. 44,211, discloses herbicidal sulfonylureas bearing ortho-phenyl groups.

EPO Pub. No. 44,209, discloses herbicidal sulfonylureas bearing --CH₂ OR and CH₂ CO₂ R₈ ortho-groups.

EPO Pub. No. 35,893, discloses herbicidal sulfonylureas bearing an ortho-sulfonyl group.

EPO Pub. No. 44,212, discloses herbicidal sulfonylureas bearing ortho-sulfonate groups.

U.S. Pat. No. 4,369,058, issued Jan. 18, 1983 discloses herbicidal sulfonylureas bearing ortho-amino substituents.

EPO Pub. No. 83,975, discloses herbicidal sulfonylureas bearing ortho-heterocyclic substituents.

EPO Pub. No. 85,476, discloses herbicidal sulfonylureas bearing ortho-pyridyl, pyrimidyl, triazinyl and furanyl groups.

South African patent application No. 83/0127 discloses herbicidal N-arylsulfonyl-N'-pyrimidinylureas of formula ##STR1## where X is optionally substituted phenyl or naphthyl.

South African patent application No. 83/0441 discloses herbicidal ureas of formula ##STR2## where X is O, S, SO or SO₂ ;

m is 0 or 1; and

Q is any of a wide variety of moieties.

South African patent application No. 83/8416 discloses herbicidal sulfonamides of formula ##STR3## where A is an unsaturated or only partially saturated 5- or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms and which may be substituted; and

R₁ is H, halo, NO₂, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ alkoxycarbonyl, C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl, C₁ -C₄ alkylsulfonyl or C₂ -C₅ alkoxyalkoxy.

SUMMARY OF THE INVENTION

Novel compounds, suitable agricultural compositions thereof and a method for their use as preemergent or postemergent herbicides or plant growth regulants have been found. The novel compounds of this invention are of the formula ##STR4## wherein R₁ is S(O)_(n) R₅, CF₃, NR₆ R₇, CO₂ R₈, SO₂ NR₉ R₁₀, ##STR5## OSO₂ R₁₃, CH₂ OR₁₄ or Q; R₂ is S(O)_(m) R₅, CF₃, NR₆ R₇, CO₂ R₈, SO₂ NR₉ R₁₀, ##STR6## OSO₂ R₁₃, CH₂ OR₁₄ or Q; R₃ is H, Cl, F, Br, CH₃, OCH₃ or CF₃ ;

R₄ is H or CH₃ ;

R₅ is C₁ -C₃ alkyl;

R₆ and R₇ are independently CH₃ or CH₂ CH₃ ;

R₈ is C₁ -C₃ alkyl, CH₂ CH═CH₂, CH₂ CH₂ Cl or CH₂ CH₂ OCH₃ ;

R₉ is CH₃ or OCH₃ ;

R₁₀ is C₁ -C₃ alkyl;

R₁₁ is H, Cl, Br, F, CH₃ or OCH₃ ;

R₁₂ is H or CH₃ ;

R₁₃ is C₁ -C₃ alkyl or CF₃ ;

R₁₄ is C₁ -C₃ alkyl or CF₂ H;

n is 0, 1 or 2;

m is 0 or 1;

Q is ##STR7## W is O, S or NR₁₈ ; W' is O or S;

R₁₅, R₁₆, R₁₇ and R₁₈ are independently H or CH₃ ;

Q is also ##STR8## R₁₉, R₂₀, R₂₂, R₂₄ and R₂₅ are independently H or CH₃ ;

R₂₁ and R₂₃ are independently H, CH₃ or OCH₃ ;

Q is also ##STR9## R₂₆, R₂₇, R₂₈ R₂₉, R₃₀ and R₃₁ are independently H or CH₃ ;

A is ##STR10## Z is CH or N; L is O or CH₂ ;

X is CH₃, OCH₃, Cl, OCH₂ CH₃, OCF₂ H or F;

Y is H, NH₂, NHCH₃, N(CH₃)₂, CH₃, CH₂ CH₃, CF₃, CH₂ OCH₃, CH₂ OCH₂ CH₃, O(C₁ -C₃ alkyl), SCH₃, O(C₃ -C₄ alkenyl), O(C₃ -C₄ alkynyl), OCH₂ CF₃, OCH₂ CH₂ F, OCH₂ CH₂ Cl, OCH₂ CH₂ Br or OCF₂ H;

X₁ is CH₃, OCH₃, Cl or OCF₂ H;

Y₁ is CH₃ or OCH₃ ;

X₂ is CH₃, CH₂ CH₃ or CH₂ CF₃ ;

Y₂ is CH₃, OCH₃ or SCH₃ ; and

Y₃ is H or CH₃ ;

and agriculturally suitable salts thereof; provided that

(a) when either one of R₁ or R₂ is CF₃, then the other is also CF₃ ;

(b) R₁ and R₂ are not simultaneously CO₂ R₈ ;

(c) when either one of R₁ or R₂ is SO₂ NR₉ R₁₀, then the other must not be S(O)_(n) R₅, S(O)_(m) R₅, CH₂ OR₁₄ or NR₆ R₇ ;

(d) when R₉ is OCH₃, then R₁₀ is CH₃ ;

(e) when either one of R₁ or R₂ is CO₂ R₈, then the other must not be S(O)_(n) R₅, S(O)_(m) R₅ or NR₆ R₇ ;

(f) the total number of carbon atoms in R₂₆ to R₃₁ combined, is equal to or less than four;

(g) when X is Cl or F, then Z is CH and Y is NH₂, NHCH₃, N(CH₃)₂, OCH₃ or OCH₂ CH₃ ;

(h) when R₁ is CO₂ R₈ and R₂ is OSO₂ R₁₃, then A is not A-1; and

(i) when X or Y is OCF₂ H and A is A-1, then R₂ is Q.

The preferred compounds of the invention for their higher herbicidal activity, greater plant growth regulant activity and/or more favorable ease of synthesis are:

(1) Compounds of Formula 1 where A is A-1; R₁ and R₂ are not simultaneously Q and R₄ is H.

(2) Compounds of Preferred 1 where Y is CH₃, CF₃, CH₂ OCH₃, OCH₃, OCH₂ CF₃ or OCF₂ H.

(3) Compounds of Preferred 2 where R₃ is in either the 3- or 5-position.

(4) Compounds of Preferred 3 where R₁ and R₂ are not simultaneously SO₂ NR₉ R₁₀ or NR₆ R₇.

(5) Compounds of Preferred 4 where R₃ is H; and at least one of R₁ or R₂ is S(O)_(n) R₅, S(O)_(m) R₅, CF₃, NR₆ R₇, SO₂ NR₉ R₁₀, ##STR11## OSO₂ R₁₃ or CH₂ OR₁₄. (6) Compounds of Preferred 5 where R₅ is CH₃ or CH₂ CH₃ ; R₆ and R₇ are both CH₃ ; R₁₀ is CH₃ ; R₁₁ is H; R₁₃ is CH₃ or CH₂ CH₃ ; and R₁₄ is CH₃.

(7) Compounds of Preferred 6 where X is CH₃, OCH₃ or Cl and Y is CH₃, OCH₃ or CH₂ OCH₃.

The most preferred compounds of the invention for their highest herbicidal activity, greatest plant growth regulating activity and/or more favorable ease of synthesis are: N-[(4,6,-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide, and N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,6-bis(methylthio)benzenesulfonamide.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The compounds of Formula (I) may be prepared by one or more of the methods described below in Equations 1 to 4. The method of choice depends on the acid or base lability of the substituents and would be obvious to one skilled in the art.

As shown in Equation 1 below, compounds of Formula I can be prepared by the reaction of an appropriately substituted sulfonamide of Formula (II) with the appropriate methyl carbamate of Formula (III) in the presence of an equimolar amount of trimethylaluminum. The reactions are best carried out at 25° to 85° in an inert solvent such as methylene chloride or 1,2-dichloroethane under an inert atmosphere. ##STR12## where R₁ or R₂ is not CO₂ R₈ ;

R₃ =H, Cl, F, Br, CH₃, OCH₃ or CF₃ ; and

R₄ is H.

Compounds of Formula (I) can also be prepared by reacting sulfonylcarbamate of Formula (IV) with an appropriate amine of Formula (V) as shown in Equation 2. The reaction is carried out at 50° to 100° in a solvent such as dioxane for 0.5 to 24 hours as taught in EPO Publication No. 44807, published Jan. 27, 1982. The required carbamates are prepared by reacting the preformed sodium salt of II with diphenylcarbonate. ##STR13## wherein R₁ or R₂ is S(O)_(n) R₅, CF₃, NR₆ R₇, SO₂ NR₉ R₁₀, C₆ H₄ R₁₁, CH₂ OR₁₄ or Q;

R₃ is as described in Equation 1; and

R₄ is H or CH₃.

Some of the compounds of Formula (I) can also be prepared as shown in Equations 3a and 3b . ##STR14##

The reaction of Equation 3acan be carried out by contacting equimolar amounts of a sulfonamide of Formula (II) with a heterocyclic phenyl carbamate of Formula (VI) in the presence of an equimolar amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), by methods analogous to those described in South African patent application No. 830441. The phenyl carbamates of Formula (VI) can be prepared by methods, or modifications thereof known to those skilled in the art, described in South African patent application No. 825671 and South African patent application No. 825045.

Rarely a sulfonamide (II) may not be of sufficient stability to be useful as a starting material in Equations 1-3a. In this case, as well as others, the sulfonyl isocyanate (VIII), can be made as an unisolated intermediate by treating the corresponding sulfonyl chloride (XV) with isocyanate anion in the presence of the heterocyclic amine (V). The amine reacts with the sulfonyl isocyanate as it is formed to give the desired compound of Formula I. ##STR15##

The reaction is best carried out by adding over one to six hours a solution of at least one equivalent of a tetraalkylammonium isocyanate, such as tetra-n-butylammonium isocyanate, in a suitable aprotic organic solvent, such as dichloromethane or tetrahydrofuran, to a well-stirred mixture of one equivalent of sulfonyl chloride (XV) and at least one equivalent of heterocyclic amine (V) in a similar suitable organic solvent at 20°-40° C. The reaction mixture is then diluted with dichloromethane, washed with 1N sulfuric acid, and dried over sodium sulfate. Rotary evaporation of the solvent leaves the product of Formula (I).

The compounds of Formula I may be prepared as shown below in Equation 4 by the reaction of an appropriate benzenesulfonyl isocyanate, VIII with an appropriate aminoheterocycle, V. ##STR16## wherein R₁, R₂, R₃ and R₄ are as described in Equation 2; and

R₁ and R₂ may also be CO₂ R₈, ##STR17## and OSO₂ R₁₃.

The reaction of Equation 4 is best carried out in an inert aprotic solvent such as methylene chloride, tetrahydrofuran or acetonitrile at a temperature between 20° and 80°. A catalytic amount of 1,4-diazabicyclo[2,2,2]octane (DABCO) may be used to accelerate the reaction. In cases in which the products are insoluble in the reaction solvent, they may be isolated by simple filtration. When the products are soluble, they may be isolated by evaporation of the solvent and trituration of the residue with solvents such as 1-chlorobutane, diethyl ether or methanol and filtration. Impure products may be purified by column chromatography on silica gel.

The benzenesulfonyl isocyanates of Formula (VIII) may be prepared as shown in Equation 5, by phosgenation of the sulfonamides (II) in the presence of butyl isocyanate. ##STR18## wherein R₁, R₂ and R₃ are as described in Equation 4.

The above reaction is carried out by heating a mixture of the appropriate sulfonamide (II), an alkyl isocyanate such as butyl isocyanate and catalytic amount of a tertiary amine such as 1,4-diazabicyclo[2,2,2]octane (DABCO) in xylene, or other inert solvent of boiling point ≧135°, to approximately 135°. Phosgene is then added to the mixture over a 1-6 hour period at 125°-135° until an excess of phosgene is present as indicated by a permanent drop in the boiling point to less than 130°. The mixture is cooled and filtered to remove a small amount of insoluble byproducts. The solvent and the alkyl isocyanate are distilled off in vacuo leaving a residue of the crude, sulfonyl isocyanate (VIII) which can be used without further purification. This method is described in U.S. Pat. No. 4,238,621.

Alternatively, the sulfonyl isocyanates (VIII) can be prepared, as shown in Equation 6, in a two-step procedure. This method is similar to a procedure taught by Ulrich and Sayrigh, New Methods of Preparative Organic Chemistry, Vol. VI, p. 223-241, Academic Press, New York and London, W. Forest Ed. ##STR19## wherein R₁, R₂ and R₃ are as described in Equation 4.

The compounds of Formula (IX) are conveniently prepared by stirring a mixture of sulfonamides (II) anhydrous potassium carbonate, and n-butyl isocyanate in a solvent such as acetone or methyl ethyl ketone at 25°-80° until all of the isocyanate has reacted. The products are isolated by quenching in dilute mineral acid and recrystallizing the solid product. The compounds (IX) are treated with phosgene and a catalytic amount of DABCO in refluxing xylene or chlorobenzene in a manner analogous to that described in Equation 5.

Sulfonyl isocyanates of Formula (VIII) may also be prepared by the procedure shown below in Equation 7 starting from the appropriate sulfonamides. ##STR20## wherein R₁, R₂ and R₃ are as described in Equation 2.

The reactions of Equation 7 are best carried out according to the procedure of Ulrich et al. in J. Org. Chem., 34, 3200 (1969). The sulfonamide is boiled under reflux with an excess of thionyl chloride which functions as both a reactant and solvent. When the sulfonamide protons are no longer detectable by proton NMR (15-20 hrs. on the average), the thionyl chloride is removed under reduced pressure and the residue is dissolved in an inert solvent such as toluene, benzene, xylenes, etc. A catalytic amount of pyridine is added. The mixture is treated with at least one equivalent of phosgene and heated to 60°-140° with 80°-100° C. preferred. Conversion to the isocyanate is substantially complete within about 1/2 to 3 hours. The mixture containing the sulfonyl isocyanate can be used directly or the sulfonyl isocyanate can be isolated in pure form by filtration and evaporation of the filtrate followed by vacuum distillation if necessary.

As shown in Equation 8 below, intermediate sulfonamides for Formula (II) can be prepared from t-butyl sulfonamides (XI). Of necessity, the reactions are limited to those cases in which R₁ is inert to lithium reagents under the conditions employed. During metallation, acids can be protected as amides and alcohols protected as tetrahydropyran ethers. For a general review of metallation with lithium reagents, see H. W. Gschwend and R. Rodriguez. Org. Reactions, 26, 1 (1979). ##STR21## where R₁ is not CH₂ CO₂ R₈, CO₂ R₈, OSO₂ R₁₃ or CH₂ OR₁₄ : ##STR22## where R₁ is as defined above;

E is R₅ SSR₅, CO₂, ##STR23## CH₂ O, CH₃ I, or CH₃ CH₂ I; and R₂ is SR₅, CO₂ H, CO₂ R₈, CH₂ OH, CH₃ or CH₂ CH₃. ##STR24## where R₁ is as defined above. ##STR25## where R₁ is as defined above; and R₂ is C₆ H₄ R₁₁ or Q. ##STR26## where R₁ is SR₅, CF₃, NR₆ R₇, CO₂ N(CH₃)₂, SO₂ NR₉ R₁₀, C₆ H₄ R₁₁, OH, CH₂ OH, Q or ##STR27## R₂ is SR₅, CO₂ H, CO₂ R₈ or CH₂ OH; and R₃ is as defined in Equation 2.

Reaction step (8a) is best carried out under nitrogen in an inert anhydrous aprotic solvent such as tetrahydrofuran, diethyl ether or hexane at temperatures between -78° and 40° C. in a manner similar to that of J. G. Lombardino [J. Org. Chem., 36, 1843 (1971)].

The preferred mode of addition is to add at least two equivalents of the alkyllithium or phenyllithium reagent to a -45° solution of the sulfonamide (XI) in tetrahydrofuran. After 15 minutes to 3 hours at room temperature, the lithium salt XIIa is obtained.

In Equation 8b, the reaction mixture is cooled to between 0° to -78° and a disulfide, carbon dioxide, chloroformate, dialkyl carbonate, formaldehyde, methyl iodide or ethyl iodide added to the lithium salt. The mixture is then allowed to warm and is stirred at ambient to reflux temperature for 6 to 20 hours. The addition of dilute acetic acid or ammonium chloride removes inorganic salts from the product contained in the organic phase to provide sulfonamides (XIIb).

In reaction 8c, XIIa is reacted with cuprous iodide at temperatures below 0° C., presumably forming XIIc. After 10 minutes to 1 hour, the aryl iodide or heterocyclic iodide is added and the mixture heated at reflux for 12 to 24 hours. After quenching the reaction with a dilute acid such as hydrochloric acid, ammonium hydroxide can be added in the presence of air to facilitate removal of the copper salts. The product may be extracted with solvents such as ethyl acetate or ether. The residue may be purified by chromatography or triturated using solvents such as hexane/chloroform or hexane/ether.

Several studies on the competition of substituents for ortho-direction capabilities indicates that for substituted sulfonamides, lithiation is directed to the position adjacent to the sulfonamide group:

D. W. Slocum and C. A. Jennings J. Org. Chem., 41, 3653 (1976);

A. I. Meyers and K. Lutomski J. Org. Chem., 44, 4464 (1979);

P. Beak and R. A. Brown J. Org. Chem., 47, 34 (1982); and

P. Beak and V. Snieckus Acc. Chem. Res., 15, 306 (1982).

For example, the metallation of (XIa) was found to occur in the 6-position. The absence of metallation at the 3 position or on the thiomethyl group attests to the powerful directing influence of the sulfonamide group and the thermodynamic stability of the resulting anion. ##STR28##

Reaction step (8e) is best carried out in trifluoroacetic acid or ethanolic hydrogen chloride between ambient and reflux temperatures for 18 to 48 hours according to the method of J. G. Lombardino [J. Org. Chem., 36, 1843 (1971)].

The deprotection appears to be concentration dependent. The yield of sulfonamide (II) can usually be increased by using a large excess of the acid as a solvent or by stripping off the by-products after 18 hours and redissolving or resuspending the residue in the acid of choice and stirring an additional 20 to 30 hours. The solvent is distilled off in vacuo and the residue can be triturated and recrystallized with solvents such as 1-chlorobutane or chloroform/hexane. The products can also be purified by chromatography.

Some sulfonamides (XIIe) are best prepared from (XIb) in a "one pot" sequence, an example of which is shown in Equation 8f. ##STR29## where R₅ and R₅ ' are independently C₁ -C₃ alkyl.

This reaction is best carried out in an inert atmosphere in an anhydrous aprotic solvent such as tetrahydrofuran, dimethylethylether or diethyl ether at temperatures between -78° and 40° C. in a manner similar to that described for Equation 8a.

The method of choice is to treat a -45° C. solution of sulfonamide (XIb) in tetrahydrofuran sequentially with (1) 2.2 equivalents of alkyllithium at -45° C. followed by warming to room temperature and stirring for 2 hours. (2) 1.0 equivalent of dialkyl disulfide at 0° C. followed by warming to ambient temperature and stirring for 2 hours. (3) 1.1 equivalent of alkyllithium at -45° C. followed by warming to room temperature and stirring for 2 hours, and (4) 1.2 equivalents of dialkyl disulfide at 0° C. followed by stirring at ambient temperature for 18 hours.

The sulfonamides of Formula (XIIg) can be prepared from compounds of Formula (XIIf) as shown in Equation 8g. ##STR30## wherein R₁ and R₃ are as described in Equation 8a;

R₁₂ is H or CH₃ ; and

R₈ is H, CH₃, CH₂ CH₃ or CH₂ CH₂ CH₃.

The above reaction is best carried out at -45° to 0° under conditions described for Equations 8a and b. The lithiation of o-toluenesulfonamides and their subsequent reactions is described by H. Watanabe and C. R. Hauser [J. Org. Chem., 33, 4278 (1968)].

The sulfonamides of Formula (XIIf) can be prepared as described in Equation 8b.

Many sulfonamides of Formula (XI) can be prepared from the corresponding sulfonyl chlorides in a manner similar to that taught by J. G. Lombardino [J. Org. Chem., 36, 1843 (1971)] as shown below. ##STR31## wherein R₁ and R₃ are as defined in Equation 2.

The reaction of Equation 8h is accomplished by treating a 0° C. solution of at least two equivalents of t-butyl amine in a solvent such as chloroform with the sulfonyl chloride (XIII). The temperature is kept at 0° to 15° C. for 1 hour then raised to 50° to 80° C. and held at that temperature for 1 to 3 hours. This mixture is then poured into cold acid such as hydrochloric acid and extracted into a solvent such as methylene chloride or ethyl ether. Products are isolated by evaporation of the solvent and trituration of the solid residues with solvents such as hexane, chloroform or 1-chlorobutane.

The sulfonyl chlorides of Formula (XIII) have been disclosed. Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene according to the teaching of H. T. Clarke et al., Org. Synth. Coll. Vol. 1, 2nd Ed., 1941, p. 85. Other benzenesulfonyl chlorides are best prepared by diazotization of the appropriate aniline with sodium nitrite in HCl, followed by reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid according to the teaching of H. L. Yale and F. Sowinski, J. Org. Chem., 25, 1824 (1960). In addition, the oxidative chlorination of mercaptans to prepare sulfonyl chlorides is widely reported in the literature, e.g., Gilbert, "Sulfonation and Related Reactions," pp. 202-214. Interscience Publishers, New York, 1965.

Sulfonamides of Formula (II) can also be prepared using the two step procedure shown in Equation 9. ##STR32## wherein R₁ or R₂ is CF₃, NR₆ R₇, SO₂ NR₉ R₁₀ or C₆ H₄ R₁₁ ; and

R₃ is as defined in Equation 2. ##STR33## wherein R₁, R₂ and R₃ are as defined above.

The reaction in Equation 9A is best carried out under nitrogen in an anhydrous, aprotic solvent such as tetrahydrofuran or diethyl ether with at least one equivalent of the alkyllithium at temperatures between -110° and -45° for 15 minutes to two hours. Sulfuryl chloride is then added and the mixture allowed to slowly warm to ambient temperature over the 1 to 4 hours. An aqueous wash removes inorganic salts and the product is obtained after evaporation of the solvent in vacuo. The crude sulfonyl chloride XV can be used without further purification. The reaction of sulfuryl chloride and phenyllithium is described by S. N. Bhattacharya et al. [J. Chem. Soc. C., 1265 (1968)].

The initial site of lithiation depends on the directing ability of the various substituents. During metallation, acids are protected as amides and phenols are protected as tetrahydropyran ethers. Benzyl alcohols may be metallated by preparing the dianion as taught by D. Seebach [Agnew. Chem. Int. Ed. Engl. 17,521 (1978)]. In general, the highest degree of lithiation occurs between the more powerful directing groups. Thus, one skilled in the art may determine which isomer will predominate.

For example, metallation at the 2-position of several 1,3-substituted benzenes has been reported: ##STR34##

The amination described in the reaction of Equation 9b is conveniently carried out by treating a solution of the sulfonyl chloride with at least two mole equivalents of anhydrous ammonia in a solvent such as ethyl ether or methylene chloride at -20° to 30° C. If the sulfonamide product II is insoluble, it may be isolated by filtration followed by washing out the salts with water. If product II is soluble in the reaction solution, it may be isolated by filtering off the precipitated ammonium chloride and evaporation of the solvent. Alternatively, many sulfonamides II can be prepared by reaction of corresponding sulfonyl chlorides IX with excess aqueous ammonium hydroxide in tetrahydrofuran at 0° to about 40° C. for 0.5 to 10 hours. The sulfonamide product II is isolated by evaporation of the tetrahydrofuran solvent, addition of water to the residue and filtration.

In some cases the sulfonamides (II) are prepared from the sulfinic acid salts (XVI). The procedure of Equation 9c is well known in the art. See U.S. Pat. No. 4,127,405 and Organic Reactions, Vol. 26, 1979, J. Wiley and Sons, Inc., N.Y. Sulfonamides (II) are best prepared by treatment of sulfinic acid salts with chloramine. In this procedure as ethereal solution or suspension of the salt (XVI) is treated at low temperatures (25° to -30°) with a dry ethereal solution of chloramine. The reaction is stirred for a period of several minutes to several hours. After filtration, the reaction mixture is washed with aqueous bisulfite and then dried and the solvent removed on a rotary evaporator. The crude product is further purified by usual methods such as crystallization or chromatography. ##STR35## wherein R₁, R₂ and R₃ are as defined in Equation 9a.

Some sulfonamides (II) can be prepared from the corresponding nitro compounds as shown in Equation 10. ##STR36## wherein R₃ is as defined in Equation 2; and

R₁₃ is C₁ -C₃ alkyl or CF₃. ##STR37## wherein R₃ and R₁₃ are as defined above. ##STR38## wherein R₃ and R₁₃ are as defined above.

Reaction step 10a is best carried out in a solvent which will also act as an acid scavenger such as pyridine at temperatures below 10° C. during the addition of methanesulfonyl chloride. After 2 to 20 hours at ambient temperature, the products can be isolated by pouring the mixture into a cold solution of acid such as hydrochloric acid and washing the resulting precipitate with dilute acid.

The reduction in Equation 10b can be run by any of several methods in the literature. For example, the reaction can be run using catalytic reduction with 10% palladium-on-charcoal in an inert solvent such as methanol or tetrahydrofuran at 25° to 45° C. at 1 to 3 atmospheres of hydrogen. For details refer to a similar procedure described by M. Vincent, et al., Bull. Soc. Chim. France, 1580 (1962).

The reaction of Equation 10c is accomplished by treating a solution of amine such as (XIX) in a mixture of concentrated hydrochloric acid and glacial acetic acid with a solution of sodium nitrite in water at -5° to 5° C. After stirring for 10-30 minutes at about 0° C. to insure complete diazotization, the solution is added to a mixture of an excess of sulfur dioxide and a catalytic amount of cuprous chloride or cupric chloride in glacial acetic acid at about 10° C. The temperature is kept at about 10° C. for 1/4 to 1 hour, then raised to 20° to 30° C. and held at that temperature for 2 to about 24 hours. This solution is then poured into a large excess of ice water. The sulfonyl chloride XV can be isolated by filtration or by extraction into a solvent such as ethyl ether, methylene chloride or preferably, 1-chlorobutane, followed by evaporation of the solvent.

The amination is conveniently carried out as described for Equation 9b to provide sulfonamide (IIa).

Several heterocyclic sulfonamides (II) are conveniently prepared from the 2,6-disubstituted nitro compounds which are commercially available or described in Beilstein: for example, 2,6-dimethyl nitrobenzene; 2-nitro-3-methyl benzoic acid; and 2-nitro-3-methyl benzaldehyde.

The heterocyclic amines of Formula (V) in Equations 1a and 3 are also important intermediates for the preparation of the compounds of this invention, which can be prepared by the following methods.

The pyrimidines and triazines of Formula (Va) to (Vd) below are either known or can be prepared by obvious methods by one skilled in the art. For instance, the synthesis of pyrimidines and triazines of the general formula (Va) has been reviewed in "The Chemistry of Heterocyclic Compounds", a series published by Interscience Publishers. Inc., New York and London. 2-Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol. 16 of this series. 2-Amino-1,3,5-triazines are reviewed by E. M. Smolin and L. Rapaport in "s-Triazines and Derivatives", Vol. 13 of the same series. The synthesis of triazines is also described by F. C. Schaefer, U.S. Pat. No. 3,154,547 and by K. R. Huffman and F. C. Schaefer, J. Org. Chem., 28, 1812 (1963). The synthesis of the bicyclic amines (Vc) and (Vd) are described in EPO Publication No. 15,683, and that of (Vb) in European Patent Publication No. 46,677. ##STR39## wherein L, X, X₁, Y and Z are as originally defined.

Heating equimolar amounts of ethyl propionimidate hydrochloride and N-aminoguanidine nitrate in pyridine gives 3-amino-5-ethyltriazole; German Patent No. 1,073,499 (1960); Berichte, 96, 1064 (1963). ##STR40##

Condensation of hydrazine with ethyl N-cyanoacetimidate yields 3-amino-5-methyltriazole; Journal of Organic Chemistry, 28, 1816 (1963). ##STR41##

British Patent No. 736,568 (1955) describes the synthesis of 3-amino-5-mercaptotriazole. ##STR42##

Condensing hydrazine with dimethyl cyanodithioimidocarbonate in acetonitrile gives 3-amino-5-methylthio-1,2,4-triazole while reaction of hydrazine with dimethyl N-cyanoimidocarbonate produces 3-amino-5-methoxy-1,2,4-triazole; Journal of Organic Chemistry, 39, 1522 (1974). ##STR43##

Reaction of substituted hydrazines with N-cyanothioimidocarbonates (prepared according to the procedure given in D. M. Wieland, Ph.D. Thesis, 1971, pp. 123-124) yields disubstituted aminotriazoles as shown below. ##STR44##

Many of the aminoheterocyclic intermediates of Formula (V) where R₄ is methyl may be prepared by a two-step procedure as described for (VI) in Equation 11. ##STR45## wherein X, Y and Z are as originally defined and

R₄ is CH₃.

A solution of the amine (XX) in concentrated hydrochloric acid is treated with sodium nitrite solution and the chloro compound (XXI) is isolated in the usual manner by filtration of the acidic solution. A representative procedure is described by Bee and Rose in J. Chem. Soc. C, 2031 (1966), for the case in which Z=CH, and X=Y=OCH₃. Displacement of the chlorine of (XXI) may be accomplished by heating with an excess of methylamine in water to obtain the methylamino heterocycle (VI).

Equation 12 below illustrates the preparation of the required methyl pyrimidinyl carbamates and methyl triazinyl carbamates of Formula (III) in Equation 1. By obvious modifications, other methyl carbamates of Formula (III) may be prepared by this method by one skilled in the art. ##STR46## wherein X, Y and Z are as originally defined; and

R₄ is H.

According to Equation 12, a heterocyclic amine is reacted with two equivalents of sodium hydride and excess dimethyl carbonate to form IIIa. The reaction is run in an inert solvent such as tetrahydrofuran at 25° C. to reflux for 1 to 24 hours. The product is isolated by (a) adding about two equivalents of concentrated hydrochloric acid under nitrogen at 0° to 30° C.; (b) filtering; and (c) separating out the organic phase, then drying (sodium sulfate and/or magnesium sulfate) and concentrating to dryness in vacuo. The product IIIa may be purified further by recrystallization or chromatography procedures.

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepard in a number of ways known to the art. For example, metal salts can be made by treating compounds of Formula I with a solution of alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of one cation to another. Cationic exchange can be effected by direct treatment of an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water, e.g., a copper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged. In this method, the cation of the resin is exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., a potassium, sodium or calcium salt.

Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is further illustrated by the following specific examples. Unless otherwise indicated, temperatures are in degrees centigrade.

EXAMPLE 1 N-[1,1-(Dimethylethyl)]-2-(methylthio)benzenesulfonamide (XIa; R₁ =SCH₃, R₃ =H)

To a mixture of 21.3 g (0.10 mol) of N-[1,1-(dimethylethyl)]benzenesulfonamide in 400 ml anhydrous tetrahydrofuran (THF) under nitrogen atmosphere was added 137 ml (0.22 mol) 1.6M butyllithium in hexanes dropwise at -40°. The mixture was then warmed to room temperature for 2 hours then recooled to -20° and treated wih 10.8 ml (0.12 mol) methyl disulfide in 15 ml THF. After stirring overnight at ambient temperature, 80 ml of 10% hydrochloric acid was added and the layers separated. The aqueous phase was extracted with ether and the combined organic extracts washed with brine, dried, and evaporated to a solid. The residue was triturated with ether/hexanes and collected to afford 23.5 g of the title compound, m.p. 138°-140°.

NMR (CDCl₃): δ 1.20 (s, 9H); 2.58 (s, 3H); 5.39 (s, NH); 7.2-7.6 (m, 4H); and 8.02-8.27 (m, 1H) ppm.

EXAMPLE 2 N-(1,1-Dimethylethyl)-2-(methylthio)-6-phenylbenzenesulfonamide (XIId; R₁ =SCH₃, R₂ =C₆ H₅, R₃ =H)

A solution of 11.3 g (0.0436 mol) N-(1,1-dimethylethyl)-2-(methylthio)benzenesulfonamide in 300 ml tetrahydrofuran (THF) was treated with 60.5 ml (0.096 mol) 2M n-butyllithium in hexanes at -30° under a nitrogen atmosphere. The mixture was stirred for 1 hour at ambient temperature then recooled to -20° and treated with 8.3 g (0.0436 mol) of cuprous iodide (anhydrous). After 10 minutes at -15°, 4.9 ml (0.0438 mol) iodobenzene was added and the mixture was then heated to reflux overnight. Acetic acid (10 ml) was added after cooling the mixture to 15°, then 200 ml concentrated ammonium hydroxide plus 200 ml ethyl acetate was introduced and the mixture was stirred vigorously in the presence of air to facilitate removal of the copper salts. The aqueous phase was separated, extracted with more ethyl acetate and the combined organic extracts were washed successively with concentrated ammonium hydroxide, water and brine, then dried (MgSO₄) and evaporated to an oil. The product crystallized from ether/hexanes to afford 10 g of material, m.p. 162°-165°.

NMR (CDCl₃): δ 1.1 (s, 9H); 2.65 (s, 3H); 5.2 (s, NH); 7.2 (t, J=4 Hz, 1H); and 7.5 (m, 7H) ppm.

EXAMPLE 3 2,6-Bis(methylthio)-N-(1,1-dimethylethyl)benzenesulfonamide (XIIb; R₁ =R₂ =SCH₃, R₃ =H)

Under nitrogen, a homogeneous solution of 80 g of N-(1,1-dimethylethyl)benzenesulfonamide in 1100 ml dry THF was cooled to -40° and 516 ml of 1.6M n-butyllithium added dropwise at this temperature. After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The resulting thick ppt. was cooled to 0° and 38 ml of methyl disulfide added dropwise. After warming to room temperature, the suspension was stirred for 1.5 hour. It was then cooled to -40° and an additional 285 ml n-butyllithium added dropwise. The suspension was allowed to warm to 25° C. and stirred at this temperature for 2 hours. Cooling to 0° and the dropwise addition of 41 ml of methyl disulfide gave a bright orange suspension. After stirring at room temperature for 18 hours, the white suspension was cooled to 0° and 20 ml of saturated ammonium chloride added dropwise. The mixture was poured into 1 l of water and extracted with ether. An insoluble precipitate remained which was collected by filtration and air dried to provide 42.3 g of 2,6-bis(methylthio)-N-(1,1-dimethylethyl)benzenesulfonamide as a white powder, m.p. 182°-185°.

The combined ether extracts were washed twice with water, once with brine and dried over sodium sulfate. Concentration gave a pale yellow solid which was washed with n-butyl chloride, providing an additional 34.5 g of the title compound, m.p. 174°-184°.

NMR (DMSO-d₆): δ 1.11 (s, 9, t-Bu); 2.48 (s, 6, SCH₃); and 7.12-7.65 (m, 4).

IR (nujol): 3.05 (NH).

EXAMPLE 4 2-(Methylthio)-6-phenylbenzenesulfonamide (II: R₁ =SCH₃, R₂ =C₆ H₅, R₃ =H)

In a mixture of 75 ml trifluoroacetic acid plus 2 ml water was dissolved 10 g (0.030 mol) of N-(1,1-dimethylethyl)-2-(methylthio)-6-phenylbenzenesulfonamide and heated to 85°. After 15 minutes the mixture was cooled and evaporated, then diluted with water and extracted with methylene chloride. The methylene chloride was washed with saturated sodium bicarbonate solution, dried (MgSO₄), evaporated in vacuo and crystallized from ether/hexanes to afford 6.5 g of the title compound, m.p. 167°-168°.

NMR (CDCl₃): δ 2.55 (s, 3H); 6.62 (2, NH₂); 7.07 (m, 1H); and 7.35-7.55 (m, 7H) ppm.

EXAMPLE 5 2-(Methylsulfonyl)-6-phenylbenzenesulfonamide (II; R₁ =SO₂ CH₃, R₂ =C₆ H₅, R₃ =H)

A solution of 6.5 g (0.023 mol) 2-(methylthio)-6-phenylbenzenesulfonamide in 100 ml methylene chloride plus 20 ml ethyl acetate was treated with 10 g (0.046 mol) 80% m-chloroperoxybenzoic acid. The mixture was subsequently stirred at ambient temperature for 3 days then filtered. The solids were rinsed with saturated sodium bicarbonate, water and more methylene chloride. A second crop was obtained from the combined bicarbonate washed methylene chloride filtrates to afford 6.9 g of the title compound, m.p. 258°-259°.

NMR (CDCl₃ /DMSO-d₆): δ 3.50 (s, 3H); 6.95 (s, NH₂); 7.47 (s, 5H); 7.5-7.98 (m, 3H); and 8.42 (m, 1H) ppm.

EXAMPLE 6 N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-3-(methylsulfonyl)-1,1'-biphenyl-2-sulfonamide (I; R₁ =SO₂ CH₃, R₂ =C₆ H₅, R₃ =R₄ =H, A=A-1, X=OCH₃, Y=CH₃, Z=CH)

To a stirred suspension of 1.2 g (3.86 mmol) 2-(methylsulfonyl)-6-phenylbenzenesulfonamide in 35 ml methylene chloride under nitrogen atmosphere was added 2.5 ml (5 mmol) of 2M trimethylaluminum in toluene via syringe at ambient temperature. Solid methyl N-(4-methoxy-6-methylpyrimidin-2-yl)carbamate (0.95 g, 4.8 mmol) was then added and the mixture was heated to reflux for 1 day. Aqueous 5% hydrochloric acid (50 ml) was added to the cooled mixture followed by ether. The solid product which separated was collected and rinsed with ether and water, then chromatographed on silica gel with 10% ethyl acetate in methylene chloride as the eluant. Trituration of the solid product with ether/hexanes afforded 0.32 g of the title compound, m.p. 206°-208°.

NMR (CDCl₃ /DMSO-d₆): δ 2.30 (s, 3H); 3.60 (s, 3H); 3.88 (s, 3H); 6.27 (s, 1H); 7.15-7.9 (m, 7H); 8.4 (sbr, NH); 8.45 (m, 1H); and 12.3 (sbr, NH) ppm.

IR (nujol): 1700, 3250 cm⁻¹.

EXAMPLE 7 2,6-Bis(methylthio)benzenesulfonamide (II; R₁ =R₂ =SCH₃ ; R₃ =H)

A brown solution of 70 g of 2,6-bis(methylthio)-N-(1,1-dimethylethyl)benzenesulfonamide in 200 ml trifluoroacetic acid was stirred at room temperature. After 10 minutes, a heavy precipitate formed, the suspension was stirred for 18 hours. The resulting solid was collected by filtration and dissolved in 10% NaOH, filtered and the filtrate acidified with 10% HCl. The precipitated solid was washed with water and air dried to provide 48 g of 2,6-bis(methylthio)benzenesulfonamide, m.p. 197°-199°.

NMR (DMSO-d₆): δ 2.48 (s, 6, SCH₃); and 7.12-7.62 (m, 5).

IR (nujol): 2.90 and 3.00 (NH₂).

EXAMPLE 8 2,6-Bis(Methylthio)-N-(butylaminocarbonyl)benzenesulfonamide (IX; R₁ =R₂ =SCH₃, R₃ =H)

A stirred suspension of 5.0 g (0.02 mol) of 2,6-bis(methylthio)benzenesulfonamide, 8.3 g (0.06 mol) potassium carbonate and 3.4 ml (0.03 mol) n-butyl isocyanate was heated at reflux for four hours. After stirring at 25° overnight, the mixture was poured into ice and 30 ml 10% HCl. The resulting precipitate was collected, washed several times with water and air dried to provide 6.5 g of the title compound, m.p. 151°-154°.

NMR (DMSO-d₆): δ 0.50-1.00 (m, 3); 1.00-1.47 (m, 4); 2.43 (s, 6); 2.67-3.15 (m, 2); 6.18-6.56 (m, 1); and 7.10-7.75 (m, 3).

IR (nujol): 3.00 (NH); and 5.95 (c=o).

EXAMPLE 9 2,6-Bis(methylthio)-N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide (I; R₁ =R₂ =SCH₃, R₃ =H, A=A-1, X=Cl, Y=OCH₃, Z=CH)

A suspension of 2.3 g (6.7 mmol) of 2,6-bis-(methylthio)-N-(butylaminocarbonyl)benzenesulfonamide and 0.07 g (0.67 mmol) of DABCO in 30 ml xylene was heated to 140°. To the resulting solution, phosgene (1.9 ml, 16 mmol) was added dropwise at 135° to 140° C. The mixture was heated at reflux for 2 hours, cooled and the solvent removed in vacuo. The resulting solid was dissolved in 50 ml methylene chloride under N₂ and 1.37 g (8.6 mmol) 2-amino-4-chloro-6-methylpyrimidine added with 0.01 g (0.1 mmol) of DABCO. The mixture was stirred overnight and the solvent removed in vacuo. The residue was triturated with 1-chlorobutane. The resulting solid was dissolved in cold 1% NaOH, filtered and precipitated with 10% HCl washed with water and air dried to provide 0.46 g of the title compound, m.p. 179°-180° C.

NMR (DMSO-d₆); δ 2.48 (s, 6, SCH₃); 4.00 (s, 3, OCH₃); 6.90 (s, 1, ArH); 7.18-7.79 (m, 3, ArH); 10.88 (brs, 1, NH); and 12.48 (brs, 1, NH).

IR (nujol): 5.80 (c=o).

Following the procedures described above, the compounds in Tables 1-15 can be prepared. In these tables, some variables are defined twice, there being a different definition when Z=CH and when Z=N. Thus, for example, in the thirteenth row in Table 3, X is defined as Cl, but, when Z=N (definition a), then X is defined as OCF₂ H. Similarly, in Table 3 and the following tables, when a row is followed by a superscript, those substituent definitions apply only when Z has the definition denoted by the superscript.

                                      TABLE 1                                      __________________________________________________________________________      ##STR47##                                                                     R.sub.1                                                                             R.sub.2                                                                            R.sub.3                                                                          A  L  X.sub.1                                                                             Y.sub.1                                                                            X.sub.2                                                                             Y.sub.2                                                                            Y.sub.3                                     __________________________________________________________________________     SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-2                                                                               O  CH.sub.3                                                                            --  --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-2                                                                               O  OCH.sub.3                                                                           --  --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-2                                                                               CH.sub.2                                                                          CH.sub.3                                                                            --  --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-2                                                                               CH.sub.2                                                                          OCH.sub.3                                                                           --  --   --  --                                          SCH.sub.3                                                                           SCH.sub.3                                                                          H A-2                                                                               O  CH.sub.3                                                                            --  --   --  --                                          SCH.sub.3                                                                           SCH.sub.3                                                                          H A-2                                                                               O  OCH.sub.3                                                                           --  --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub. 6 H.sub.5                                                                   H A-2                                                                               O  Cl   --  --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-2                                                                               O  OCF.sub.2 H                                                                         --  --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-3                                                                               -- CH.sub.3                                                                            --  --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-3                                                                               -- OCH.sub.3                                                                           --  --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-3                                                                               -- Cl   --  --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-3                                                                               -- OCF.sub.2 H                                                                         --  --   --  --                                          SCH.sub.3                                                                           SCH.sub.3                                                                          H A-3                                                                               -- OCH.sub.3                                                                           --  --   --  --                                          SCH.sub.3                                                                           SCH.sub.3                                                                          H A-3                                                                               -- CH.sub.3                                                                            --  --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-4                                                                               -- CH.sub.3                                                                            --  --   --  CH.sub.3                                    SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-4                                                                               -- OCH.sub.3                                                                           --  --   --  CH.sub.3                                    SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-4                                                                               -  Cl   --  --   --  H                                           SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-4                                                                               -- OCF.sub.2 H                                                                         --  --   --  CH.sub.3                                    SCH.sub.3                                                                           SCH.sub.3                                                                          H A-4                                                                               -- OCH.sub.3                                                                           --  --   --  CH.sub.3                                    SCH.sub.3                                                                           SCH.sub.3                                                                          H A-4                                                                               -- CH.sub.3                                                                            --  --   --  H                                           SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-5                                                                               -- --   CH.sub.3                                                                           --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-5                                                                               -- --   OCH.sub.3                                                                          --   --  --                                          SCH.sub.3                                                                           SCH.sub.3                                                                          H A-5                                                                               -- --   CH.sub.3                                                                           --   --  --                                          SCH.sub.3                                                                           SCH.sub.3                                                                          H A-5                                                                               -- --   OCH.sub.3                                                                          --   --  --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-6                                                                               -- --   --  CH.sub.3                                                                            CH.sub.3                                                                           --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-6                                                                               -- --   --  CH.sub.3                                                                            OCH.sub.3                                                                          --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-6                                                                               -- --   --  CH.sub.3                                                                            SCH.sub.3                                                                          --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-6                                                                               -- --   --  CH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-6                                                                               -- --   --  CH.sub.2 CH.sub.3                                                                   OCH.sub.3                                                                          --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-6                                                                               -- --   --  CH.sub.2 CH.sub.3                                                                   SCH.sub.3                                                                          --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-6                                                                               -- --   --  CH.sub.2 CF.sub.3                                                                   CH.sub.3                                                                           --                                          SO.sub.2 CH.sub.3                                                                   C.sub.6 H.sub.5                                                                    H A-6                                                                               -- --   --  CH.sub.2 CF.sub.3                                                                   OCH.sub.3                                                                          --                                          SCH.sub.3                                                                           SCH.sub.3                                                                          H A-6                                                                               -- --   --  CH.sub.3                                                                            CH.sub.3                                                                           --                                          SCH.sub.3                                                                           SCH.sub.3                                                                          H A-6                                                                               -- --   --  CH.sub.3                                                                            OCH.sub.3                                                                          --                                          __________________________________________________________________________

                                      TABLE 2a                                     __________________________________________________________________________      ##STR48##                                                                                                               m.p.                                 R.sub.1     R.sub.2     R.sub.3                                                                            X     Y       (°C.)                         __________________________________________________________________________     SCH.sub.3   SCH.sub.2 CH.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    SCH.sub.2 CH.sub.3                                                                         SCH.sub.2 CH.sub.3                                                                         3-Cl                                                                               CH.sub.3                                                                             OCH.sub.3                                    SCH.sub.2 CH.sub.3                                                                         SCH.sub.2 CH.sub.2 CH.sub.3                                                                H   OCH.sub.3                                                                            OCH.sub.3                                    SCH.sub.2 CH.sub.2 CH.sub.3                                                                SCH.sub.2 CH.sub.2 CH.sub.3                                                                H   CH.sub.3                                                                             OCH.sub.3                                    S(O)CH.sub.3                                                                               SCH.sub.3   H   CH.sub.3                                                                             CH.sub.3                                     S(O).sub.2 CH.sub.3                                                                        SCH.sub.3   H   CH.sub.3                                                                             OCH.sub.3                                    S(O)CH.sub.3                                                                               S(O)CH.sub.3                                                                               H   OCH.sub.3                                                                            OCH.sub.3                                    S(O).sub.2 CH.sub.3                                                                        S(O)CH.sub.3                                                                               H   Cl    OCH.sub.3                                    SCH.sub.3   N(CH.sub.3).sub.2                                                                          H   CH.sub.3                                                                             OCH.sub.3                                    S(O)CH.sub.3                                                                               N(CH.sub.3).sub.2                                                                          H   OCH.sub.3                                                                            OCH.sub.3                                    S(O).sub.2 CH.sub.3                                                                        N(CH.sub.3).sub.2                                                                          H   Cl    OCH.sub.3                                    SCH.sub.3   N(CH.sub.3)CH.sub.2 CH.sub.3                                                               3-F CH.sub.3                                                                             OCH.sub.3                                    SCH.sub.3   N(CH.sub.2 CH.sub.3).sub.2                                                                 H   OCH.sub.3                                                                            OCH.sub.3                                    CF.sub.3    CF.sub.3    H   CH.sub.3                                                                             OCH.sub.3                                    CF.sub.3    CF.sub.3    4-Br                                                                               CH.sub.3                                                                             CH.sub.3                                     N(CH.sub.3).sub.2                                                                          N(CH.sub.3).sub.2                                                                          H   CH.sub.3                                                                             OCH.sub.3                                    N(CH.sub.3)CH.sub.2 CH.sub.3                                                               N(CH.sub.3).sub.2                                                                          H   OCH.sub.3                                                                            OCH.sub.3                                    N(CH.sub.2 CH.sub.3).sub.2                                                                 N(CH.sub.3).sub.2                                                                          4-CH.sub.3                                                                         CH.sub.3                                                                             OCH.sub.3                                    N(CH.sub.3)CH.sub.2 CH.sub.3                                                               N(CH.sub.3)CH.sub.2 CH.sub.3                                                               H   OCH.sub.3                                                                            OCH.sub.3                                    N(CH.sub.2 CH.sub.3).sub.2                                                                 N(CH.sub.2 CH.sub.3).sub.2                                                                 H   Cl    OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          C.sub.6 H.sub.5                                                                            H   CH.sub.3                                                                             OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          2'-C.sub.6 H.sub.4 Cl                                                                      H   Cl    OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.3                                                                 H   CH.sub.3                                                                             CH.sub.3                                     N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                        H   CH.sub.3                                                                             OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                               H   Cl    OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.2 CHCH.sub.2                                                      H   OCH.sub.3                                                                            OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                     5-OCH.sub.3                                                                        CH.sub.3                                                                             CH.sub.3                                     N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                              H   CH.sub.3                                                                             CH.sub.3                                     N(CH.sub.3).sub.2                                                                           ##STR49##  H   CH.sub.3                                                                             OCH.sub.3                                    N(CH.sub.3).sub.2                                                                           ##STR50##  H   OCH.sub.3                                                                            OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          OSO.sub.2 CH.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          OSO.sub.2 CH.sub.2 CH.sub.3                                                                3-CF.sub.3                                                                         Cl    OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       H   CH.sub.3                                                                             OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          OSO.sub.2 CF.sub.3                                                                         H   OCH.sub.3                                                                            OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          CH.sub.2 OCH.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          CH.sub.2 OCH.sub.2 CH.sub.3                                                                H   CH.sub.3                                                                             CH.sub.3                                     N(CH.sub.3).sub.2                                                                          CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3                                                       H   OCH.sub.3                                                                            OCH.sub.3                                    N(CH.sub.3).sub.2                                                                          CH.sub.2 OCF.sub.2 H                                                                       H   CH.sub.3                                                                             OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                          SO.sub.2 N(CH.sub.3).sub.2                                                                 H   CH.sub.3                                                                             OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                          SO.sub.2 N(CH.sub.3)OCH.sub.3                                                              H   CH.sub.3                                                                             CH.sub.3                                     CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                 H   OCH.sub.3                                                                            OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   CH.sub.3                                                                             OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                          2'-C.sub.6 H.sub.4 OCH.sub.3                                                               H   OCH.sub.3                                                                            OCH.sub.3                                    CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        3'-C.sub.6 H.sub.4 CH.sub.3                                                                H   CH.sub.3                                                                             CH.sub.3                                     CO.sub.2 CH.sub.3                                                                          CH.sub.2 CO.sub.2 CH.sub.3                                                                 H   CH.sub.3                                                                             OCH.sub.3                                    CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                               ##STR51##  H   OCH.sub.3                                                                            OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                          CH.sub.2 OCF.sub.2 H                                                                       H   OCH.sub.3                                                                            OCH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                                 SO.sub.2 N(CH.sub.3).sub.2                                                                 H   CH.sub.3                                                                             CH.sub.3                                     SO.sub.2 N(CH.sub.3)OCH.sub.3                                                              SO.sub.2 N(CH.sub.3).sub.3                                                                 H   CH.sub.3                                                                             OCH.sub.3                                    SO.sub.2 N(CH.sub.3)OCH.sub.3                                                              SO.sub.2 N(CH.sub.3)OCH.sub.3                                                              H   CH.sub.3                                                                             CH.sub.3                                     SO.sub.2 N(CH.sub.3).sub.2                                                                 C.sub.6 H.sub.5                                                                            H   OCH.sub.3                                                                            OCH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                                 4'-C.sub.6 H.sub.4 Cl                                                                      H   CH.sub.3                                                                             OCH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                                 2'-C.sub.6 H.sub.4 OCH.sub.3                                                               H   OCH.sub.3                                                                            OCH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 CO.sub.2 CH.sub.3                                                                 H   CH.sub.3                                                                             OCH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                                  ##STR52##  H   CH.sub.3                                                                             CH.sub.3                                     SO.sub.2 N(CH.sub.3).sub.2                                                                 OSO.sub.2 CH.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                                 OSO.sub.2 CF.sub.3                                                                         H   OCH.sub.3                                                                            OCH.sub.3                                    C.sub.6 H.sub.5                                                                            C.sub.6 H.sub.5                                                                            H   CH.sub.3                                                                             OCH.sub.3                                    C.sub.6 H.sub.5                                                                            2'-C.sub.6 H.sub.4 Cl                                                                      H   OCH.sub.3                                                                            OCH.sub.3                                    C.sub.6 H.sub.5                                                                            3'-C.sub.6 H.sub.4 Cl                                                                      H   CH.sub.3                                                                             OCH.sub.3                                     ##STR53##                                                                                  ##STR54##  H   OCH.sub.3                                                                            OCH.sub.3                                     ##STR55##                                                                                  ##STR56##  H   CH.sub.3                                                                             CH.sub.3                                     C.sub.6 H.sub.5                                                                            CH.sub.2 CO.sub.2 CH.sub.3                                                                 H   CH.sub.3                                                                             OCH.sub.3                                    C.sub.6 H.sub.5                                                                             ##STR57##  H   OCH.sub.3                                                                            OCH.sub.3                                    2'-C.sub.6 H.sub.4 CH.sub.3                                                                CH.sub.2 CO.sub.2 CH.sub.3                                                                 H   Cl    OCH.sub.3                                    C.sub.6 H.sub.5                                                                            OSO.sub.2 CH.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    C.sub.6 H.sub.5                                                                            OSO.sub.2 CF.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    2'-C.sub.6 H.sub.4 F                                                                       OSO.sub.2 CH.sub.2 CH.sub.3                                                                H   OCH.sub.3                                                                            OCH.sub.3                                    C.sub.6 H.sub.5                                                                            CH.sub.2 OCH.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    4'-C.sub.6 H.sub.4 Cl                                                                      CH.sub.2 OCF.sub.2 H                                                                       H   CH.sub.3                                                                             OCH.sub.3                                    CH.sub.2 CO.sub.2 CH.sub.3                                                                 CH.sub.2 CO.sub. 2 CH.sub.3                                                                3-CH.sub.3                                                                         CH.sub.3                                                                             OCH.sub.3                                    CH.sub.2 CO.sub.2 CH.sub.3                                                                 CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                     H   CH.sub.3                                                                             OCH.sub.3                                    CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                              CH.sub.2 CO.sub.2 CH.sub.2 CHCH.sub.2                                                      H   CH.sub.3                                                                             OCH.sub.3                                     ##STR58##  CH.sub.2 CO.sub.2 CH.sub.3                                                                 H   OCH.sub.3                                                                            OCH.sub.3                                     ##STR59##  CH.sub.2 CO.sub.2 CH.sub.3                                                                 H   CH.sub.3                                                                             CH.sub.3                                      ##STR60##                                                                                  ##STR61##  H   OCH.sub.3                                                                            CH.sub.3                                     CH.sub.2 CO.sub.2 CH.sub.3                                                                 OSO.sub.2 CH.sub.3                                                                         H   OCH.sub.3                                                                            OCH.sub.3                                     ##STR62##  OSO.sub.2 CF.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    CH.sub.2 CO.sub.2 CH.sub.3                                                                 CH.sub.2 OCH.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                     ##STR63##  CH.sub.2 OCF.sub.2 H                                                                       H   CH.sub.3                                                                             CH.sub.3                                     OSO.sub.2 CH.sub.3                                                                         OSO.sub.2 CH.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    OSO.sub.2 CF.sub.3                                                                         OSO.sub.2 CH.sub.3                                                                         H   CH.sub.3                                                                             CH.sub.3                                     OSO.sub.2 CF.sub.3                                                                         OSO.sub.2 CF.sub.3                                                                         H   CH.sub.3                                                                             CH.sub.3                                     OSO.sub.2 CH.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                         4-CF.sub.3                                                                         CH.sub.3                                                                             OCH.sub.3                                    OSO.sub.2 CF.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                         H   OCH.sub.3                                                                            OCH.sub.3                                    OSO.sub.2 CH.sub.3                                                                         CH.sub.2 OCF.sub.2 H                                                                       H   CH.sub.3                                                                             OCH.sub.3                                    OSO.sub.2 CF.sub.3                                                                         CH.sub.2 OCF.sub.2 H                                                                       5-Cl                                                                               CH.sub.3                                                                             CH.sub.3                                     CH.sub.2 OCH.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                         H   CH.sub.3                                                                             OCH.sub.3                                    CH.sub.2 OCF.sub.2 H                                                                       CH.sub.2 OCH.sub.3                                                                         H   OCH.sub.3                                                                            OCH.sub.3                                    CH.sub.2 OCF.sub.2 H                                                                       CH.sub.2 OCF.sub.2 H                                                                       H   CH.sub.3                                                                             CH.sub.3                                     SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   CH.sub.3                                                                             CH.sub.3                                                                               228-230° d                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   CH.sub.3                                                                             OCH.sub.3                                                                              206-208° d                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   CH    CF.sub.3                                     SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   CH.sub.3                                                                             CH.sub.2 OCH.sub.3                           SO.sub.2 CH.sub. 3                                                                         C.sub.6 H.sub.5                                                                            3-Cl                                                                               CH.sub.3                                                                             CH.sub.2 OCH.sub.3                           SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             CH.sub.3                                                                               188-194°                      SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             OCH.sub.3                                                                              206-208°                      SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             CF.sub.3                                     SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             H                                            SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             NH.sub.2                                     SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             NHCH.sub.3                                   SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             N(CH.sub.3).sub.2                            SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             CH.sub.2 CH.sub.3                            SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             CH.sub.2 OCH.sub.2 CH.sub.3                  SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             OCH.sub.2 CH.sub.3                           SCH.sub.3   SCH.sub.3   5-CF.sub.3                                                                         CH.sub.3                                                                             OCH.sub.2 CH.sub.3                           SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             SCH.sub.3                                    SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             OCH.sub.2 CHCH.sub.2                         SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             OCH.sub.2 CCH                                SCH.sub.3   SCH.sub.3   H   CH.sub.3                                                                             OCH.sub.2 CH.sub.2 F                         SCH.sub.3   C.sub.6 H.sub.5                                                                            H   CH.sub.3                                                                             OCH.sub.2 CH.sub.2 Cl                        SCH.sub.3   C.sub.6 H.sub.5                                                                            H   CH.sub.3                                                                             OCH.sub.2 CH.sub.2 Br                        SCH.sub.3   SCH.sub.3   3-Cl                                                                               CH.sub.3                                                                             OCH.sub.3                                    SCH.sub.3   SCH.sub.3   3-CH.sub.3                                                                         CH.sub.3                                                                             OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                          2'-C.sub.6 H.sub.4 Cl                                                                      H   CH.sub.3                                                                             OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            3-Cl                                                                               CH.sub.3                                                                             OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            5-Cl                                                                               CH.sub.3                                                                             OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   OCH.sub.3                                                                            CF.sub.3                                     SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                           SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   OCH.sub.3                                                                            OCH.sub.3                                                                              212-214°                      SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                           SCH.sub.3   SCH.sub.3   H   OCH.sub.3                                                                            CF.sub.3                                     SCH.sub.3   SCH.sub.3   H   OCH.sub.3                                                                            OCH.sub.3                                                                              220-225°                      SCH.sub.3   SCH.sub.3   H   OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                           SCH.sub.3   SCH.sub.3   3-Cl                                                                               CH.sub.3                                                                             OCH.sub.3                                    SCH.sub.3   SCH.sub.3   3-OCH.sub.3                                                                        OCH.sub.3                                                                            OCH.sub.3                                    SCH.sub.3   SCH.sub.3   H   OCH.sub.3                                                                            N(CH.sub.3).sub.2                            SCH.sub.3   SCH.sub.3   H   OCH.sub.3                                                                            CH.sub.2 CH.sub.3                            SCH.sub.3   SCH.sub.3   H   OCH.sub.3                                                                            SCH.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   Cl    NH.sub.2                                     SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   Cl    NHCH.sub.3                                   SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   Cl    N(CH.sub.3).sub.2                            SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   Cl    OCH.sub.3                                    SCH.sub.3   SCH.sub.3   H   Cl    OCH.sub.3                                                                              179-186°                      SCH.sub.3   SCH.sub.3   H   Cl    N(CH.sub.3).sub.2                            SCH.sub.3   SCH.sub.3   3-Cl                                                                               CH.sub.3                                                                             OCH.sub.3                                    SCH.sub.3   SCH.sub.3   3-CH.sub.3                                                                         OCH.sub.3                                                                            OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   OCH.sub.2 CH.sub.3                                                                   H                                            SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                     SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   OCH.sub.2 CH.sub.3                                                                   CF.sub.3                                     SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   OCH.sub.2 CH.sub.3                                                                   CH.sub.2 OCH.sub.3                           SCH.sub.3   SCH.sub.3   H   OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                     SCH.sub.3   SCH.sub.3   H   OCH.sub.2 CH.sub.3                                                                   CF.sub.3                                     SCH.sub.3   SCH.sub.3   3-OCH.sub.3                                                                        OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                     SO.sub.2 CH.sub.3                                                                          C.sub. 6 H.sub.5                                                                           H   F     OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   F     NH.sub.2                                     SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   F     NHCH.sub.3                                   SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H   F     N(CH.sub.3).sub.2                            SCH.sub.3   SCH.sub.3   H   F     OCH.sub.3                                    SCH.sub.3   SCH.sub.3   H   F     N(CH.sub.3).sub.2                            SCH.sub.3   C.sub.6 H.sub.5                                                                            H   CH.sub.3                                                                             CH.sub.3                                                                               218-221° d                    SCH.sub.3   C.sub.6 H.sub.5                                                                            H   CH.sub.3                                                                             OCH.sub.3                                                                              170-173°                      SCH.sub.3   C.sub.6 H.sub.5                                                                            H   OCH.sub.3                                                                            OCH.sub.3                                                                              187-189°                      __________________________________________________________________________

                                      TABLE 2b                                     __________________________________________________________________________      ##STR64##                                                                                                                 m.p.                               R.sub.1     R.sub.2     R.sub.3                                                                             X     Y        (°C.)                       __________________________________________________________________________     SCH.sub.3   SCH.sub.2 CH.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   SCH.sub.2 CH.sub.3                                                                         SCH.sub.2 CH.sub.3                                                                         3-Cl CH.sub.3                                                                             OCH.sub.3                                   SCH.sub.2 CH.sub.3                                                                         SCH.sub.2 CH.sub.2 CH.sub.3                                                                H    OCH.sub.3                                                                            OCH.sub.3                                   SCH.sub.2 CH.sub.2 CH.sub.3                                                                SCH.sub.2 CH.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                             OCH.sub.3                                   S(O)CH.sub.3                                                                               SCH.sub.3   H    CH.sub.3                                                                             CH.sub.3                                    S(O).sub.2 CH.sub.3                                                                        SCH.sub.3   H    CH.sub.3                                                                             OCH.sub.3                                   S(O)CH.sub.3                                                                               S(O)CH.sub.3                                                                               H    OCH.sub.3                                                                            OCH.sub.3                                   S(O).sub.2 CH.sub.3                                                                        S(O)CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                   SCH.sub.3   N(CH.sub.3).sub.2                                                                          H    CH.sub.3                                                                             OCH.sub. 3                                  S(O)CH.sub.3                                                                               N(CH.sub.3).sub.2                                                                          H    OCH.sub.3                                                                            OCH.sub.3                                   S(O).sub.2 CH.sub.3                                                                        N(CH.sub.3).sub.2                                                                          H    CH.sub.3                                                                             OCH.sub.3                                   SCH.sub.3   N(CH.sub.3)CH.sub.2 CH.sub.3                                                               3-F  CH.sub.3                                                                             OCH.sub.3                                   SCH.sub.3   N(CH.sub.2 CH.sub.3).sub.2                                                                 H    OCH.sub.3                                                                            OCH.sub.3                                   CF.sub.3    CF.sub.3    H    CH.sub.3                                                                             OCH.sub.3                                   CF.sub.3    CF.sub.3    4-Br CH.sub.3                                                                             CH.sub.3                                    N(CH.sub.3).sub.2                                                                          N(CH.sub.3).sub.2                                                                          H    CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3)CH.sub.2 CH.sub.3                                                               N(CH.sub.3).sub.2                                                                          H    OCH.sub.3                                                                            OCH.sub.3                                   N(CH.sub.2 CH.sub.3).sub.2                                                                 N(CH.sub.3).sub.2                                                                          4-CH.sub.3                                                                          CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3)CH.sub.2 CH.sub.3                                                               N(CH.sub.3)CH.sub.2 CH.sub.3                                                               H    OCH.sub.3                                                                            OCH.sub.3                                   N(CH.sub.2 CH.sub.3).sub.2                                                                 N(CH.sub.2 CH.sub.3).sub.2                                                                 H    CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          C.sub.6 H.sub.5                                                                            H    CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          2'-C.sub.6 H.sub.4 Cl                                                                      H    CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.3                                                                 H    CH.sub.3                                                                             CH.sub.3                                    N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                        H    CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                               H    OCH.sub.3                                                                            OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.2 CHCH.sub.2                                                      H    OCH.sub.3                                                                            OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                     5-OCH.sub.3                                                                         CH.sub.3                                                                             CH.sub.3                                    N(CH.sub.3).sub.2                                                                          CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                              H    CH.sub.3                                                                             CH.sub.3                                    N(CH.sub.3).sub.2                                                                           ##STR65##  H    CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3).sub.2                                                                           ##STR66##  H    OCH.sub.3                                                                            OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          OSO.sub.2 CH.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          OSO.sub.2 CH.sub.2 CH.sub.3                                                                3-CF.sub.3                                                                          CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          OSO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       H    CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          OSO.sub.2 CF.sub.3                                                                         H    OCH.sub.3                                                                            OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          CH.sub.2 OCH.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   N(CH.sub.3 ).sub.2                                                                         CH.sub.2 OCH.sub.2 CH.sub.3                                                                H    CH.sub.3                                                                             CH.sub.3                                    N(CH.sub.3).sub.2                                                                          CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.3                                                       H    OCH.sub.3                                                                            OCH.sub.3                                   N(CH.sub.3).sub.2                                                                          CH.sub.2 OCF.sub.2 H                                                                       H    CH.sub.3                                                                             OCH.sub.3                                   CO.sub.2 CH.sub.3                                                                          SO.sub.2 N(CH.sub.3).sub.2                                                                 H    CH.sub.3                                                                             OCH.sub.3                                   CO.sub.2 CH.sub.3                                                                          SO.sub.2 N(CH.sub.3)OCH.sub.3                                                              H    CH.sub.3                                                                             CH.sub.3                                    CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              SO.sub.2 N(CH.sub.3).sub.2                                                                 H    OCH.sub.3                                                                            OCH.sub.3                                   CO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    CH.sub.3                                                                             OCH.sub.3                                   CO.sub.2 CH.sub.3                                                                          2'-C.sub.6 H.sub.4 OCH.sub.3                                                               H    OCH.sub.3                                                                            OCH.sub.3                                   CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        3'-C.sub.6 H.sub.4 CH.sub.3                                                                H    CH.sub.3                                                                             CH.sub.3                                    CO.sub.2 CH.sub.3                                                                          CH.sub.2 CO.sub.2 CH.sub.3                                                                 H    CH.sub.3                                                                             OCH.sub.3                                   CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                               ##STR67##  H    OCH.sub.3                                                                            OCH.sub.3                                   CO.sub.2 CH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   CO.sub.2 CH.sub.3                                                                          CH.sub.2 OCF.sub. 2 H                                                                      H    OCH.sub.3                                                                            OCH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                 SO.sub.2 N(CH.sub.3).sub.2                                                                 H    CH.sub.3                                                                             CH.sub.3                                    SO.sub.2 N(CH.sub.3)OCH.sub.3                                                              SO.sub.2 N(CH.sub.3).sub.3                                                                 H    CH.sub.3                                                                             OCH.sub.3                                   SO.sub.2 N(CH.sub.3)OCH.sub.3                                                              SO.sub.2 N(CH.sub.3)OCH.sub.3                                                              H    CH.sub.3                                                                             CH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                                 C.sub.6 H.sub.5                                                                            H    OCH.sub.3                                                                            OCH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                 4'-C.sub.6 H.sub.4 Cl                                                                      H    CH.sub.3                                                                             OCH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                 2'-C.sub.6 H.sub.4 OCH.sub.3                                                               H    OCH.sub.3                                                                            OCH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.2 CO.sub.2 CH.sub.3                                                                 H    CH.sub.3                                                                             OCH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                  ##STR68##  H    CH.sub.3                                                                             CH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                                 OSO.sub.2 CH.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                                 OSO.sub.2 CF.sub.3                                                                         H    OCH.sub.3                                                                            OCH.sub.3                                   C.sub.6 H.sub.5                                                                            C.sub.6 H.sub.5                                                                            H    CH.sub.3                                                                             OCH.sub.3                                   C.sub.6 H.sub.5                                                                            2'-C.sub.6 H.sub.4 Cl                                                                      H    OCH.sub.3                                                                            OCH.sub.3                                   C.sub.6 H.sub.5                                                                            3'-C.sub.6 H.sub.4 Cl                                                                      H    CH.sub.3                                                                             OCH.sub.3                                    ##STR69##                                                                                  ##STR70##  H    OCH.sub.3                                                                            OCH.sub.3                                    ##STR71##                                                                                  ##STR72##  H    CH.sub.3                                                                             CH.sub.3                                    C.sub.6 H.sub.5                                                                            CH.sub.2 CO.sub.2 CH.sub.3                                                                 H    CH.sub.3                                                                             OCH.sub.3                                   C.sub.6 H.sub.5                                                                             ##STR73##  H    OCH.sub.3                                                                            OCH.sub.3                                   2'-C.sub.6 H.sub.4 CH.sub.3                                                                CH.sub.2 CO.sub.2 CH.sub.3                                                                 H    CH.sub.3                                                                             OCH.sub.3                                   C.sub.6 H.sub.5                                                                            OSO.sub.2 CH.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   C.sub.6 H.sub.5                                                                            OSO.sub.2 CF.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   2'-C.sub.6 H.sub.4 F                                                                       OSO.sub.2 CH.sub.2 CH.sub.3                                                                H    OCH.sub.3                                                                            OCH.sub.3                                   C.sub.6 H.sub.5                                                                            CH.sub.2 OCH.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   4'-C.sub.6 H.sub.4 Cl                                                                      CH.sub.2 OCF.sub.2 H                                                                       H    CH.sub.3                                                                             OCH.sub.3                                   CH.sub.2 CO.sub.2 CH.sub.3                                                                 CH.sub.2 CO.sub.2 CH.sub.3                                                                 3-CH.sub.3                                                                          CH.sub.3                                                                             OCH.sub.3                                   CH.sub.2 CO.sub.2 CH.sub.3                                                                 CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                     H    CH.sub.3                                                                             OCH.sub.3                                   CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                              CH.sub.2 CO.sub.2 CH.sub.2 CHCH.sub.2                                                      H    CH.sub.3                                                                             OCH.sub.3                                    ##STR74##  CH.sub.2 CO.sub.2 CH.sub.3                                                                 H    OCH.sub.3                                                                            OCH.sub.3                                    ##STR75##  CH.sub.2 CO.sub.2 CH.sub.3                                                                 H    CH.sub.3                                                                             CH.sub.3                                     ##STR76##                                                                                  ##STR77##  H    OCH.sub.3                                                                            CH.sub.3                                    CH.sub.2 CO.sub.2 CH.sub.3                                                                 OSO.sub.2 CH.sub.3                                                                         H    OCH.sub.3                                                                            OCH.sub.3                                    ##STR78##  OSO.sub.2 CF.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   CH.sub.2 CO.sub.2 CH.sub.3                                                                 CH.sub.2 OCH.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                    ##STR79##                                                                                 CH.sub.2 OCF.sub.2 H                                                                       H    CH.sub.3                                                                             CH.sub.3                                    OSO.sub.2 CH.sub.3                                                                         OSO.sub.2 CH.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   OSO.sub.2 CF.sub.3                                                                         OSO.sub.2 CH.sub.3                                                                         H    CH.sub.3                                                                             CH.sub.3                                    OSO.sub.2 CF.sub.3                                                                         OSO.sub.2 CF.sub.3                                                                         H    CH.sub.3                                                                             CH.sub.3                                    OSO.sub.2 CH.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                         4-CF.sub.3                                                                          CH.sub.3                                                                             OCH.sub.3                                   OSO.sub.2 CF.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                         H    OCH.sub.3                                                                            OCH.sub.3                                   OSO.sub.2 CH.sub.3                                                                         CH.sub.2 OCF.sub.2 H                                                                       H    CH.sub.3                                                                             OCH.sub.3                                   OSO.sub.2 CF.sub.3                                                                         CH.sub.2 OCF.sub.2 H                                                                       5-Cl CH.sub.3                                                                             CH.sub.3                                    CH.sub.2 OCH.sub.3                                                                         CH.sub.2 OCH.sub.3                                                                         H    CH.sub.3                                                                             OCH.sub.3                                   CH.sub.2 OCF.sub.2 H                                                                       CH.sub.2 OCH.sub.3                                                                         H    OCH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 OCF.sub.2 H                                                                       CH.sub.2 OCF.sub.2 H                                                                       H    CH.sub.3                                                                             CH.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    CH.sub.3                                                                             CH.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    CH.sub.3                                                                             OCH.sub.3                                                                               204-208° d.                 SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    CH    CF.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    CH.sub. 3                                                                            CH.sub.2 OCH.sub.3                          SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            3-Cl CH.sub.3                                                                             CH.sub.2 OCH.sub.3                          SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    CH.sub.3                                                                             OCH.sub.2 CF.sub.3                          SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             CH.sub.3 179-193°                    SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             OCH.sub.3                                   SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             CF.sub.3                                    SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             H                                           SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             NH.sub.2                                    SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             NHCH.sub.3                                  SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             N(CH.sub.3).sub.2                           SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             CH.sub.2 CH.sub.3                           SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             CH.sub.2 OCH.sub.2 CH.sub.3                 SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             OCH.sub.2 CH.sub.3                          SCH.sub.3   SCH.sub.3   5-CF.sub.3                                                                          CH.sub.3                                                                             OCH.sub.2 CH.sub.3                          SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             SCH.sub.3                                   SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             OCH.sub.2 CHCH.sub.2                        SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             OCH.sub.2 CCH                               SCH.sub.3   SCH.sub.3   H    CH.sub.3                                                                             OCH.sub.2 CH.sub. 2 F                       SCH.sub.3   C.sub.6 H.sub.5                                                                            H    CH.sub.3                                                                             OCH.sub.2 CH.sub.2 Cl                       SCH.sub.3   C.sub.6 H.sub.5                                                                            H    CH.sub.3                                                                             OCH.sub.2 CH.sub.2 Br                       SCH.sub.3   SCH.sub.3   3-Cl CH.sub.3                                                                             OCH.sub.3                                   SCH.sub.3   SCH.sub.3   3-CH.sub.3                                                                          CH.sub.3                                                                             OCH.sub.3                                   SO.sub.2 CH.sub.3                                                                          2'-C.sub.6 H.sub.4 Cl                                                                      H    CH.sub.3                                                                             OCH.sub.3                                   SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            3-Cl CH.sub.3                                                                             OCH.sub.3                                   SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            5-Cl CH.sub.3                                                                             OCH.sub.3                                   SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    OCH.sub.3                                                                            CF.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                          SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    OCH.sub.3                                                                            OCH.sub.3                                                                               216-220° d.                 SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                          SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                            CF.sub.3                                    SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                            OCH.sub.3                                                                               121-132°                    SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                          SCH.sub.3   SCH.sub.3   3-Cl CH.sub.3                                                                             OCH.sub.3                                   SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                            N(CH.sub.3 ).sub.2                          SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                            CH.sub.2 CH.sub.3                           SCH.sub.3   SCH.sub.3   H    OCH.sub.3                                                                            SCH.sub.3                                   SCH.sub.3   SCH.sub.3   3-Cl CH.sub.3                                                                             OCH.sub.3                                   SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    OCH.sub.2 CH.sub.3                                                                   H                                           SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    OCH.sub.2 CH.sub.3                                                                   CF.sub.3                                    SO.sub.2 CH.sub.3                                                                          C.sub.6 H.sub.5                                                                            H    OCH.sub.2 CH.sub.3                                                                   CH.sub.2 OCH.sub.3                          SCH.sub.3   SCH.sub.3   H    OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                    SCH.sub.3   SCH.sub.3   H    OCH.sub.2 CH.sub.3                                                                   CF.sub.3                                    SCH.sub.3   SCH.sub.3   3-OCH.sub.3                                                                         OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                    SCH.sub.3   C.sub.6 H.sub.5                                                                            H    OCH.sub.3                                                                            CH.sub.3 130-135° d.                 __________________________________________________________________________

                  TABLE 3                                                          ______________________________________                                          ##STR80##                                                                     Z = (a.) N or (b.) CH                                                          R.sub.1    R.sub.2     R.sub.3   X     Y                                       ______________________________________                                         SCH.sub.3  SCH.sub.2 CH.sub.3                                                                         H         CH.sub.3                                                                             CH.sub.3                                SCH.sub.3  SCH.sub.2 CH.sub.3                                                                         H         CH.sub.3                                                                             OCH.sub.3                               SCH.sub.3  SCH.sub.2 CH.sub.3                                                                         5-CF.sub.3                                                                               CH.sub.3                                                                             OCH.sub.3                               SCH.sub.3  SCH.sub.2 CH.sub.3                                                                         H         OCH.sub.3                                                                            OCH.sub.3                               SCH.sub.3  SCH.sub.2 CH.sub.3                                                                         3-Cl      OCH.sub.3                                                                            OCH.sub.3                               SCH.sub.3  SCH.sub.2 CH.sub.2 CH.sub.3                                                                H         CH.sub.3                                                                             OCH.sub.3                               SCH.sub.3  SCH.sub.2 CH.sub.2 CH.sub.3                                                                H         OCH.sub.3                                                                            OCH.sub.3                               SCH.sub.2 CH.sub.2 CH.sub.3                                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                H         CH.sub.3                                                                             OCH.sub.3                               SCH.sub.2 CH.sub.2 CH.sub.3                                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                H         OCH.sub. 3                                                                           OCH.sub.3                               SCH.sub.2 CH.sub.2 CH.sub.3                                                               SCH.sub.2 CH.sub.2 CH.sub.3                                                                4-OCH.sub.3                                                                              CH.sub.3                                                                             OCH.sub.3                               S(O)CH.sub.3                                                                              SCH.sub.3   H         CH.sub.3                                                                             OCH.sub.3                               S(O)CH.sub.3                                                                              S(O)CH.sub.3                                                                               H         OCH.sub.3                                                                            OCH.sub.3                               S(O).sub.2 CH.sub.3                                                                       S(O)CH.sub.3                                                                               H         Cl.sup.b                                                                             OCH.sub.3                               N(CH.sub.3).sub.2                                                                         C.sub.6 H.sub.5                                                                            H         CH.sub.3                                                                             CH.sub.3                                N(CH.sub.3).sub.2                                                                         C.sub.6 H.sub.5                                                                            H         CH.sub.3                                                                             OCH.sub.3                               N(CH.sub.3).sub.2                                                                         C.sub.6 H.sub.5                                                                            H         OCH.sub.3                                                                            OCH.sub.3                               N(CH.sub.3).sub.2                                                                         C.sub.6 H.sub.5                                                                            H         Cl.sup.b                                                                             OCH.sub.3                               N(CH.sub.3).sub.2                                                                         N(CH.sub.3).sub.2                                                                          H         CH.sub.3                                                                             OCH.sub.3                               N(CH.sub.3).sub.2                                                                         N(CH.sub.3).sub.2                                                                          H         OCH.sub.3                                                                            OCH.sub.3                               N(CH.sub.3).sub.2                                                                         N(CH.sub.3).sub.2                                                                          H         Cl.sup.b                                                                             OCH.sub.3                               CF.sub.3   CF.sub.3    H         CH.sub.3                                                                             CH.sub.3                                CF.sub.3   CF.sub.3    H         CH.sub.3                                                                             OCH.sub.3                               CF.sub.3   CF.sub.3    H         OCH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                            H         CH.sub.3                                                                             OCH.sub.3                               CO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                            H         OCH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                            H         Cl.sup.b                                                                             OCH.sub.3                               OSO.sub.2 N(CH.sub.3).sub.2                                                               C.sub.6 H.sub.5                                                                            H         CH.sub.3                                                                             OCH.sub.3                               OSO.sub.2 N(CH.sub.3).sub.2                                                               C.sub.6 H.sub.5                                                                            H         OCH.sub.3                                                                            OCH.sub.3                               C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                            H         CH.sub.3                                                                             CH.sub.3                                C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                            H         CH.sub.3                                                                             OCH.sub.3                               C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                            H         OCH.sub.3                                                                            OCH.sub.3                               OSO.sub.2 CH.sub.3                                                                        C.sub.6 H.sub.5                                                                            H         CH.sub.3                                                                             OCH.sub.3                               OSO.sub.2 CH.sub.3                                                                        C.sub.6 H.sub.5                                                                            H         OCH.sub.3                                                                            OCH.sub.3                               OSO.sub.2 CH.sub.3                                                                        OSO.sub.2 CH.sub.3                                                                         H         CH.sub.3                                                                             CH.sub.3                                OSO.sub.2 CH.sub.3                                                                        OSO.sub.2 CH.sub.3                                                                         H         CH.sub.3                                                                             OCH.sub.3                               OSO.sub.2 CH.sub.3                                                                        OSO.sub.2 CH.sub.3                                                                         H         OCH.sub.3                                                                            OCH.sub.3                               SCH.sub.3  N(CH.sub.3).sub.2                                                                          H         CH.sub.3                                                                             CH.sub.3                                SCH.sub.3  N(CH.sub.3).sub.2                                                                          H         CH.sub.3                                                                             OCH.sub.3                               SCH.sub.3  N(CH.sub.3).sub.2                                                                          H         OCH.sub.3                                                                            OCH.sub.3                               S(O)CH.sub.3                                                                              N(CH.sub.3).sub.2                                                                          H         OCH.sub.3                                                                            OCH.sub.3                               S(O).sub.2 CH.sub.3                                                                       N(CH.sub.3).sub.2                                                                          H         OCH.sub.3                                                                            OCH.sub.3                               ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                          ##STR81##                                                                     R.sub.1    R.sub.3                                                                               R.sub.15                                                                              R.sub.16                                                                            R.sub.17                                                                             X     Y                                    ______________________________________                                         SCH.sub.3  H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H      H      H    H     OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H      CH.sub.3                                                                              H    H     CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H      H      H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H      CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                             SCH.sub.2 CH.sub.3                                                                        H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            SCH.sub.2 CH.sub.2 CH.sub.3                                                               H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H      H      H    H     CH.sub.3                                                                             CH.sub.3                             S(O)CH.sub.3                                                                              H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H      CH.sub.3                                                                              H    H     Cl    OCH.sub.3 .sup.b                     S(O)CH.sub.3                                                                              H      H      H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      H      H    H     OCH.sub.3                                                                            OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      CH.sub.3                                                                              H    H     CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      H      H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H      H      H    H     CH.sub.3                                                                             CH.sub.3                             CF.sub.3   H      CH.sub.3                                                                              H    H     OCH.sub.3                                                                            CH.sub.3                             CF.sub.3   H      H      CH.sub.3                                                                            H     OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H      CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      H      H    H     OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      CH.sub.3                                                                              H    H     CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      H      CH.sub.3                                                                            H     OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.2 CH.sub.3).sub. 2                                                               H      H      H    H     OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      CH.sub.3                                                                              H    H     OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      H      CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                             CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                                H      H      H    H     OCH.sub.3                                                                            OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                                H      CH.sub.3                                                                              H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      H      H    H     OCH.sub.3                                                                            OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      CH.sub.3                                                                              H    CH.sub.3                                                                             CL    OCH.sub.3 .sup.b                     C.sub.6 H.sub.5                                                                           H      H      CH.sub.3                                                                            H     CH.sub.3                                                                             OCH.sub.3                            2'-C.sub.6 H.sub.4 Cl                                                                     H      H      H    H     OCH.sub.3                                                                            OCH.sub.3                            2'-C.sub.6 H.sub.4 CH.sub.3                                                               H      H      H    H     OCF.sub.2 H                                                                          OCH.sub.3                            2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            3'-C.sub.6 H.sub.4 F                                                                      H      CH.sub.3                                                                              H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            4'-C.sub.6 H.sub.4 Br                                                                     H      CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                             Cl    OCH.sub.3 .sup.b                     CH.sub.2 CO.sub.2 CH.sub.3                                                                H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      CH.sub.3                                                                              H    H     OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      H      CH.sub.3                                                                            H     Cl    OCH.sub.3 .sup.b                      ##STR82##                                                                     OSO.sub.2 CH.sub.3                                                                        H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                        H      CH.sub.3                                                                              H    H     OCH.sub.3                                                                            OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                        H      H      CH.sub.3                                                                            CH.sub.3                                                                             Cl    OCH.sub.3 .sup.b                     OSO.sub.2 CH.sub.3                                                                        H      CH.sub.3                                                                              CH.sub.3                                                                            H     OCH.sub.3                                                                            OCF.sub.2 H                          OSO.sub.2 CF.sub.3                                                                        H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      H      H    H     CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      CH.sub.3                                                                              H    H     OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      H      CH.sub.3                                                                            H     OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCH.sub.3                                                                        H      CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                             CH.sub.2 OCF.sub.2 H                                                                      H      H      H    H     OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                      H      CH.sub.3                                                                              H    CH.sub.3                                                                             OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCF.sub.2 H                                                                      H      H      CH.sub.3                                                                            H     Cl    OCH.sub.3 .sup.b                     CH.sub.2 OCF.sub.2 H                                                                      H      CH.sub.3                                                                              CH.sub.3                                                                            H     CH.sub.3                                                                             OCH.sub.3                            ______________________________________                                    

                                      TABLE 5                                      __________________________________________________________________________     (a.) Z = N (b.) Z = CH                                                                    ##STR83##                                                           (c.) Z = N (d.) Z = CH                                                                    ##STR84##                                                           (e.) Z =  N (f.) Z = CH                                                                   ##STR85##                                                           R.sub.1   R.sub.3                                                                            W    R.sub.15                                                                           R.sub.16                                                                           X   Y                                               __________________________________________________________________________     SCH.sub.3 H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.3 H   O    H   H   OCH.sub.3                                                                          OCH.sub.3                                       SCH.sub.3 H   O    H   CH.sub.3                                                                           H   OCH.sub.3                                       SCH.sub.3 H   O    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       SCH.sub.3 H   O    CH.sub.3                                                                           H   CH.sub.3                                                                           CH.sub.3                                        SCH.sub.3 3-CH.sub.3                                                                         O    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        SCH.sub.2 CH.sub.3                                                                       H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.2 CH.sub.2 CH.sub.3                                                              H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       S(O)CH.sub. 3                                                                            H   O    H   H   CH.sub.3                                                                           CH.sub.3                                        S(O)CH.sub.3                                                                             H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       S(O)CH.sub.3                                                                             H   O    CH.sub.3                                                                           H   Cl.sup.b,d,f                                                                       OCH.sub.3                                       S(O)CH.sub.3                                                                             H   O    H   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       S(O).sub.2 CH.sub.3                                                                      H   O    H   H   OCH.sub.3                                                                          OCH.sub.3                                       S(O).sub.2 CH.sub.3                                                                      H   O    CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       S(O).sub.2 CH.sub.3                                                                      H   O    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       CF.sub.3  H   O    H   H   CH.sub.3                                                                           CH.sub.3                                        CF.sub.3  H   O    CH.sub.3                                                                           H   OCH.sub.3                                                                          CH.sub.3                                        CF.sub.3  H   O    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       CF.sub.3  H   O    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   O    H   H   OCH.sub.3                                                                          OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   O    CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   O    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.2 CH.sub.3).sub.2                                                               H   O    H   H   OCH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H   O    CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H   O    H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                               H   O    H   H   OCH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 N(CH3).sub.2                                                                    H   O    CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   O    H   H   CH.sub.3                                                                           CH.sub.3                                        C.sub.6 H.sub.5                                                                          H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   O    H   H   OCH.sub.3                                                                          OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   O    CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   O    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   O    CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                          OCF.sub.2 H                                     2'-C.sub.6 H.sub.4 Cl                                                                    H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H   O    H   H   OCH.sub.3                                                                          OCH.sub.3                                       2'-C.sub.6 H.sub.4 CH.sub.3                                                              H   O    H   H   Cl.sup. b,d,f                                                                      OCH.sub.3                                       3'-C.sub.6 H.sub.4 Br                                                                    H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       4'-C.sub.6 H.sub.4 F                                                                     H   O    H   H   OCH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H   O    CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H   O    H   CH.sub.3                                                                           Cl.sup.b,d,f                                                                       OCH.sub.3                                        ##STR86##                                                                               H   O    H   H   OCH.sub.3                                                                          OCF.sub.2 H                                     OSO.sub.2 CH.sub.3                                                                       H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                       H   O    CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                       H   O    H   CH.sub.3                                                                           Cl.sup.b,d,f                                                                       OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                       H   O    CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                          OCF.sub.2 H                                     OSO.sub.2 CF.sub.3                                                                       H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       CH.sub.2 OCH.sub.3                                                                       H   O    H   H   CH.sub.3                                                                           OCH.sub.3                                       CH.sub.2 OCH.sub.3                                                                       H   O    CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 OCH.sub.3                                                                       H   O    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCF.sub.2 H                                     CH.sub.2 OCH.sub.3                                                                       H   O    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        CH.sub.2 OCF.sub.2 H                                                                     H   O    H   H   OCH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 OCF.sub.2 H                                                                     H   O    CH.sub.3                                                                           H   OCH.sub.3                                                                          OCF.sub.2 H                                     CH.sub.2 OCF.sub.2 H                                                                     H   O    H   CH.sub.3                                                                           Cl.sup.b,d,f                                                                       OCH.sub.3                                       CH.sub.2 OCF.sub.2 H                                                                     H   O    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.3 H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.3 H   NCH.sub.3                                                                           H   H   OCH.sub.3                                                                          OCH.sub.3                                       SCH.sub.3 H   NCH.sub.3                                                                           CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.3 H   NCH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       SCH.sub.3 H   NH   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        SCH.sub.3 3-OCH.sub.3                                                                        NCH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.2 CH.sub.3                                                                       H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.2 CH.sub.2 CH.sub.3                                                              H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       S(O)CH.sub.3                                                                             H   NH   H   H   CH.sub.3                                                                           CH.sub.3                                        S(O)CH.sub.3                                                                             H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       S(O)CH.sub.3                                                                             H   NCH.sub.3                                                                           CH.sub.3                                                                           H   Cl.sup.b,d,f                                                                       OCH.sub.3                                       S(O)CH.sub.3                                                                             H   NCH.sub.3                                                                           H   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       S(O).sub.2 CH.sub.3                                                                      H   NCH.sub.3                                                                           H   H   OCH.sub.3                                                                          OCH.sub.3                                       S(O).sub.2 CH.sub.3                                                                      H   NCH.sub.3                                                                           CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       S(O).sub.2 CH.sub.3                                                                      H   NCH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       CF.sub.3  H   NH   H   H   CH.sub.3                                                                           CH.sub.3                                        CF.sub.3  H   NCH.sub.3                                                                           CH.sub.3                                                                           H   OCH.sub.3                                                                          CH.sub.3                                        CF.sub.3  H   NCH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       CF.sub.3  H   NH   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   NCH.sub.3                                                                           H   H   OCH.sub.3                                                                          OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   NCH.sub.3                                                                           CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   NCH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.2 CH.sub.3).sub.2                                                               H   NCH.sub.3                                                                           H   H   OCH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H   NCH.sub.3                                                                           CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H   NCH.sub.3                                                                           H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                               H   NCH.sub.3                                                                           H   H   OCH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                               H   NH   CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           CH.sub.3                                        C.sub.6 H.sub.5                                                                          H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   NCH.sub.3                                                                           H   H   OCH.sub.3                                                                          OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   NCH.sub.3                                                                           CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   NCH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   NCH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                          OCF.sub.2 H                                     2'-C.sub.6 H.sub.4 Cl                                                                    H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H   NCH.sub.3                                                                           H   H   OCH.sub.3                                                                          OCH.sub.3                                       2'-C.sub.6 H.sub.4 CH.sub.3                                                              H   NCH.sub.3                                                                           H   H   Cl.sup.b,d,f                                                                       OCH.sub.3                                       3'-C.sub.6 H.sub.4 Br                                                                    H   NH   H   H   CH.sub.3                                                                           OCH.sub.3                                       4'-C.sub.6 H.sub.4 F                                                                     H   NCH.sub.3                                                                           H   H   OCH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H   NCH.sub.3                                                                           CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H   NCH.sub.3                                                                           H   CH.sub.3                                                                           Cl.sup.b,d,f                                                                       OCH.sub.3                                        ##STR87##                                                                               H   NCH.sub.3                                                                           H   H   OCH.sub.3                                                                          OCF.sub.2 H                                     OSO.sub.2 CH.sub.3                                                                       H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                       H   NCH.sub.3                                                                           CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                       H   NCH.sub.3                                                                           H   CH.sub.3                                                                           Cl.sup.b,d,f                                                                       OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                       H   NCH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                          OCF.sub.2 H                                     OSO.sub.2 CF.sub.3                                                                       H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       CH.sub.2 OCH.sub.3                                                                       H   NCH.sub.3                                                                           H   H   CH.sub.3                                                                           OCH.sub.3                                       CH.sub.2 OCH.sub.3                                                                       H   NCH.sub.3                                                                           CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 OCh.sub.3                                                                       H   NH   H   CH.sub.3                                                                           OCH.sub.3                                                                          OCF.sub. 2 H                                    CH.sub.2 OCH.sub.3                                                                       H   NCH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        CH.sub.2 OCF.sub.2 H                                                                     H   NCH.sub.3                                                                           H   H   OCH.sub.3                                                                          OCH.sub.3                                       Ch.sub.2 OCF.sub.2 H                                                                     H   NCH.sub.3                                                                           CH.sub.3                                                                           H   OCH.sub.3                                                                          OCF.sub.2 H                                     CH.sub.2 OCF.sub.2 H                                                                     H   NCH.sub.3                                                                           H   CH.sub.3                                                                           OCF.sub.2 H                                                                        OCH.sub.3                                       CH.sub.2 OCF.sub.2 H                                                                     H   NCH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.3 H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.3 H   S    H   H   OCH.sub.3                                                                          OCH.sub.3                                       SCH.sub.3 H   S    CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.3 H   S    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCh.sub.3                                       SCH.sub.3 H   S    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        SCH.sub.3 3-Cl                                                                               S    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.2 CH.sub.3                                                                       H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       SCH.sub.2 CH.sub.2 CH.sub.3                                                              H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       S(O)CH.sub.3                                                                             H   S    H   H   CH.sub.3                                                                           CH.sub.3                                        S(O)CH.sub.3                                                                             H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       S(O)CH.sub.3                                                                             H   S    CH.sub.3                                                                           H   Cl.sup. b,d,f                                                                      OCH.sub.3                                       S(O)CH.sub.3                                                                             H   S    H   CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       S(O).sub.2 CH.sub.3                                                                      H   S    H   H   OCH.sub.3                                                                          OCH.sub.3                                       S(O).sub.2 CH.sub.3                                                                      H   S    CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       S(O).sub.2 CH.sub.3                                                                      H   S    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       CF.sub.3  H   S    H   H   CH.sub.3                                                                           CH.sub.3                                        CF.sub.3  H   S    CH.sub.3                                                                           H   OCH.sub.3                                                                          CH.sub.3                                        CF.sub.3  H   O    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       CF.sub.3  H   S    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   S    H   H   OCH.sub.3                                                                          OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   S    CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.3).sub.2                                                                        H   S    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       N(CH.sub.2 CH.sub.3).sub.2                                                               H   S    H   H   OCH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H   S    CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H   S    H   CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                            H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                               H   S    H   H   OCH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                               H   S    CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   S    H   H   CH.sub.3                                                                           CH.sub.3                                        C.sub.6 H.sub.5                                                                          H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   S    H   H   OCH.sub.3                                                                          OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   S    CH.sub.3                                                                           H   CH.sub.3                                                                           OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   S    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCH.sub.3                                       C.sub.6 H.sub.5                                                                          H   S    CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                          OCF.sub.2 H                                     2'-C.sub.6 H.sub.4 Cl                                                                    H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       2'-C.sub.6 H.sub.4 OCH.sub.3                                                             H   S    H   H   OCH.sub.3                                                                          OCH.sub.3                                       2'-C.sub.6 H.sub.4 CH.sub.3                                                              H   S    H   H   Cl.sup.b,d,f                                                                       OCH.sub.3                                       3'-C.sub.6 H.sub.4 Br                                                                    H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       4'-C.sub.6 H.sub.4 F                                                                     H   S    H   H   OCH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H   S    CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 CO.sub.2 CH.sub.3                                                               H   S    H   CH.sub.3                                                                           OCF.sub.2 H                                                                        OCH.sub.3                                        ##STR88##                                                                               H   S    H   H   OCH.sub.3                                                                          OCF.sub.2 H                                     OSO.sub.2 CH.sub.3                                                                       H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                       H   S    CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                       H   S    H   CH.sub.3                                                                           Cl.sup.b,d,f                                                                       OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                       H   S    CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                          OCF.sub.2 H                                     OSO.sub.2 CF.sub.3                                                                       H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       CH.sub.2 OCH.sub.3                                                                       H   S    H   H   CH.sub.3                                                                           OCH.sub.3                                       CH.sub.2 OCH.sub.3                                                                       H   S    CH.sub.3                                                                           H   OCH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 OCH.sub.3                                                                       H   S    H   CH.sub.3                                                                           OCH.sub.3                                                                          OCF.sub.2 H                                     CH.sub.2 OCH.sub.3                                                                       H   S    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                        CH.sub.2 OCF.sub.2 H                                                                     H   S    H   H   OCH.sub.3                                                                          OCH.sub. 3                                      CH.sub.2 OCF.sub.2 H                                                                     H   S    CH.sub.3                                                                           H   OCH.sub.3                                                                          OCF.sub.2 H                                     CH.sub.2 OCF.sub.2 H                                                                     H   S    H   CH.sub.3                                                                           Cl.sup.b,d,f                                                                       OCH.sub.3                                       CH.sub.2 OCF.sub.2 H                                                                     H   S    CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                       __________________________________________________________________________

                  TABLE 6                                                          ______________________________________                                         R.sub.1     R.sub.3                                                                              W'      R.sub.15                                                                            X        Y                                      ______________________________________                                         SCH.sub.3   H     O       H    CH.sub.3 OCH.sub.3                              SCH.sub.3   H     O       H    OCH.sub.3                                                                               OCH.sub.3                              SCH.sub.3   H     O       CH.sub.3                                                                            CH.sub.3 OCH.sub.3                              SCH.sub.3   H     O       CH.sub.3                                                                            CH.sub.3 CH.sub.3                               SCH.sub.2 CH.sub.3                                                                         H     O       H    CH.sub.3 OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub.3                                                                H     O       H    CH.sub.3 OCH.sub.3                              S(O)CH.sub.3                                                                               H     O       H    CH.sub.3 CH.sub.3                               S(O)CH.sub.3                                                                               H     O       H    CH.sub.3 OCH.sub.3                              S(O)CH.sub.3                                                                               H     O       CH.sub.3                                                                            Cl       OCH.sub.3.sup.b,d,f                    S(O).sub.2 CH.sub.3                                                                        H     O       H    OCH.sub.3                                                                               OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                        H     O       H    CH.sub.3 OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                        H     O       CH.sub.3                                                                            OCH.sub.3                                                                               OCH.sub.3                              CF.sub.3    H     O       H    CH.sub.3 CH.sub.3                               CF.sub.3    H     O       H    OCH.sub.3                                                                               OCH.sub.3                              CF.sub.3    H     O       CH.sub.3                                                                            CH.sub.3 OCH.sub.3                              N(CH.sub.3).sub.2                                                                          H     O       H    CH.sub.3 OCH.sub.3                              N(CH.sub.3).sub.2                                                                          H     O       H    OCH.sub.3                                                                               OCH.sub.3                              N(CH.sub.3).sub.2                                                                          H     O       CH.sub.3                                                                            CH.sub.3 OCH.sub.3                              N(CH.sub.3)CH.sub.2 CH.sub.3                                                               H     O       H    CH.sub.3 OCH.sub.3                              N(CH.sub.2 CH.sub.3).sub.2                                                                 H     O       H    OCH.sub.3                                                                               OCH.sub.3                              CO.sub.2 CH.sub.3                                                                          H     O       H    CH.sub.3 OCH.sub.3                              CO.sub.2 CH.sub.3                                                                          H     O       H    OCH.sub.3                                                                               OCH.sub.3                              CO.sub.2 CH.sub.3                                                                          H     O       CH.sub.3                                                                            CH.sub.3 CH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              H     O       H    CH.sub.3 OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                                 H     O       H    OCH.sub.3                                                                               OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                                 H     O       CH.sub.3                                                                            CH.sub.3 OCH.sub.3                              C.sub.6 H.sub.5                                                                            H     O       H    CH.sub.3 CH.sub.3                               C.sub.6 H.sub.5                                                                            H     O       H    CH.sub.3 OCH.sub.3                              C.sub.6 H.sub.5                                                                            H     O       H    OCH.sub.3                                                                               OCH.sub.3                              C.sub.6 H.sub.5                                                                            H     O       CH.sub.3                                                                            OCH.sub.3                                                                               OCH.sub.3                              2'-C.sub.6 H.sub.4 Cl                                                                      H     O       H    CH.sub.3 OCH.sub.3                              2'-C.sub.6 H.sub.4 CH.sub.3                                                                H     O       H    OCH.sub.3                                                                               OCH.sub.3                              2'-C.sub.6 H.sub.4 OCH.sub.3                                                               H     O       H    OCF.sub.2 H                                                                             OCH.sub.3                              3'-C.sub.6 H.sub.4 Br                                                                      H     O       H    CH.sub.3 OCH.sub.3                              4'-C.sub.6 H.sub.4 F                                                                       H     O       H    Cl       OCH.sub.3.sup.b,d,f                    CH.sub.2 CO.sub.2 CH.sub.3                                                                 H     O       H    CH.sub.3 OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                 H     O       H    OCH.sub.3                                                                               OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                 H     O       CH.sub.3                                                                            Cl       OCH.sub.3.sup.b,d,f                     ##STR89##  H     O       H    OCH.sub.3                                                                               OCF.sub.2 H                            OSO.sub.2 CH.sub.3                                                                         H     O       H    CH.sub.3 OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                         H     O       H    OCH.sub.3                                                                               OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                         H     O       CH.sub.3                                                                            Cl       OCH.sub.3.sup.b,d,f                    OSO.sub.2 CH.sub.3                                                                         H     O       CH.sub.3                                                                            OCH.sub.3                                                                               OCF.sub.2 H                            OSO.sub.2 CF.sub.3                                                                         H     O       H    CH.sub.3 OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                         H     O       H    CH.sub.3 OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                         H     O       H    OCH.sub.3                                                                               OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                         H     O       CH.sub.3                                                                            OCH.sub.3                                                                               OCF.sub.2 H                            CH.sub.2 OCH.sub.3                                                                         H     O       CH.sub.3                                                                            CH.sub.3 CH.sub.3                               CH.sub.2 OCF.sub.2 H                                                                       H     O       H    OCH.sub. 3                                                                              OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                       H     O       H    OCH.sub.3                                                                               OCF.sub.2 H                            CH.sub.2 OCF.sub.2 H                                                                       H     O       CH.sub.3                                                                            Cl       OCH.sub.3.sup.b,d,f                    CH.sub.2 OCF.sub.2 H                                                                       H     O       CH.sub.3                                                                            CH.sub.3 OCH.sub.3                              SCH.sub.3   H     S       H    CH.sub.3 OCH.sub.3                              SCH.sub.3   H     S       H    OCH.sub.3                                                                               OCH.sub.3                              SCH.sub.3   H     S       CH.sub.3                                                                            CH.sub.3 OCH.sub.3                              SCH.sub.3   H     S       CH.sub.3                                                                            CH.sub.3 CH.sub.3                               SCH.sub.2 CH.sub.3                                                                         H     S       H    CH.sub.3 OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub.3                                                                H     S       H    CH.sub.3 OCH.sub.3                              S(O)CH.sub.3                                                                               H     S       H    CH.sub.3 CH.sub.3                               S(O)CH.sub.3                                                                               H     S       H    CH.sub.3 OCH.sub.3                              S(O)CH.sub.3                                                                               H     S       CH.sub.3                                                                            Cl       OCH.sub.3.sup.b,d,f                    S(O).sub.2 CH.sub.3                                                                        H     S       H    OCH.sub.3                                                                               OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                        H     S       H    CH.sub.3 OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                        H     S       CH.sub.3                                                                            OCH.sub.3                                                                               OCH.sub.3                              CF.sub.3    H     S       H    CH.sub.3 CH.sub.3                               CF.sub.3    H     O       H    OCH.sub.3                                                                               OCH.sub.3                              CF.sub.3    H     S       CH.sub.3                                                                            CH.sub.3 OCH.sub.3                              N(CH.sub.3).sub.2                                                                          H     S       H    CH.sub.3 OCH.sub.3                              N(CH.sub.3).sub.2                                                                          H     S       H    OCH.sub.3                                                                               OCH.sub.3                              N(CH.sub.3).sub.2                                                                          H     S       CH.sub.3                                                                            CH.sub.3 OCH.sub.3                              N(CH.sub.3)CH.sub.2 CH.sub.3                                                               H     S       H    CH.sub.3 OCH.sub.3                              N(CH.sub.2 CH.sub.3).sub.2                                                                 H     S       H    OCH.sub.3                                                                               OCH.sub.3                              CO.sub.2 CH.sub.3                                                                          H     S       H    CH.sub.3 OCH.sub.3                              CO.sub.2 CH.sub.3                                                                          H     S       H    OCH.sub.3                                                                               OCH.sub.3                              CO.sub.2 CH.sub.3                                                                          H     S       CH.sub.3                                                                            CH.sub.3 CH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              H     S       H    CH.sub.3 OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                                 H     S       H    OCH.sub.3                                                                               OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                                 H     S       CH.sub.3                                                                            CH.sub.3 OCH.sub.3                              C.sub.6 H.sub.5                                                                            H     S       H    CH.sub.3 CH.sub.3                               C.sub.6 H.sub.5                                                                            H     S       H    CH.sub.3 OCH.sub.3                              C.sub.6 H.sub.5                                                                            H     S       H    OCH.sub.3                                                                               OCH.sub.3                              C.sub.6 H.sub.5                                                                            H     S       CH.sub.3                                                                            OCH.sub.3                                                                               OCH.sub.3                              2'-C.sub.6 H.sub.4 Cl                                                                      H     S       H    CH.sub.3 OCH.sub.3                              2'-C.sub.6 H.sub.4 CH.sub.3                                                                H     S       H    OCH.sub.3                                                                               OCH.sub. 3                             2'-C.sub.6 H.sub.4 OCH.sub.3                                                               H     S       H    OCF.sub.2 H                                                                             OCH.sub.3                              3'-C.sub.6 H.sub.4 Br                                                                      H     S       H    CH.sub.3 OCH.sub.3                              4'-C.sub.6 H.sub.4 F                                                                       H     S       H    Cl       OCH.sub.3.sup.b,d,f                    CH.sub.2 CO.sub.2 CH.sub.3                                                                 H     S       H    CH.sub.3 OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                 H     S       H    OCH.sub.3                                                                               OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                 H     S       CH.sub.3                                                                            Cl       OCH.sub.3.sup.b,d,f                     ##STR90##  H     S       H    OCH.sub.3                                                                               OCF.sub.2 H                            OSO.sub.2 CH.sub.3                                                                         H     S       H    CH.sub.3 OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                         H     S       H    OCH.sub.3                                                                               OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                         H     S       CH.sub.3                                                                            Cl       OCH.sub.3.sup.b,d,f                    OSO.sub.2 CH.sub.3                                                                         H     S       CH.sub.3                                                                            OCH.sub.3                                                                               OCF.sub.2 H                            OSO.sub.2 CF.sub.3                                                                         H     S       H    CH.sub.3 OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                         H     S       H    CH.sub.3 OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                         H     S       H    OCH.sub.3                                                                               OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                         H     S       CH.sub.3                                                                            OCH.sub.3                                                                               OCF.sub.2 H                            CH.sub.2 OCH.sub.3                                                                         H     S       CH.sub.3                                                                            CH.sub.3 CH.sub.3                               CH.sub.2 OCF.sub.2 H                                                                       H     S       H    OCH.sub.3                                                                               OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                       H     S       H    OCH.sub.3                                                                               OCF.sub.2 H                            CH.sub.2 OCF.sub.2 H                                                                       H     S       CH.sub.3                                                                            Cl       OCH.sub.3.sup.b,d,f                    CH.sub.2 OCF.sub.2 H                                                                       H     S       CH.sub.3                                                                            CH.sub.3 OCH.sub.3                              ______________________________________                                          .sup.a Z = N                                                                   .sup.b Z = CH                                                                  ##STR91##                                                                      .sup.c Z = N                                                                   .sup.d Z = CH                                                                  ##STR92##                                                                      .sup.e Z = N                                                                   .sup.f Z = CH                                                                  ##STR93##                                                                

                  TABLE 7                                                          ______________________________________                                         R.sub.1       R.sub.3                                                                              R.sub.15 X      Y                                          ______________________________________                                         SCH.sub.3     H     H        CH.sub.3                                                                              OCH.sub.3                                  SCH.sub.3     H     H        OCH.sub.3                                                                             OCH.sub.3                                  SCH.sub.3     H     CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                  SCH.sub.3     H     CH.sub.3 CH.sub.3                                                                              CH.sub.3                                   SCH.sub.2 CH.sub.3                                                                           H     H        CH.sub.3                                                                              OCH.sub.3                                  SCH.sub.2 CH.sub.2 CH.sub.3                                                                  H     H        CH.sub.3                                                                              OCH.sub.3                                  S(O)CH.sub.3  H     H        CH.sub.3                                                                              CH.sub.3                                   S(O)CH.sub.3  H     H        CH.sub.3                                                                              OCH.sub.3                                  S(O)CH.sub.3  H     CH.sub.3 Cl     OCH.sub.3.sup.b,d                          S(O).sub.2 CH.sub.3                                                                          H     H        OCH.sub.3                                                                             OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                          H     H        CH.sub.3                                                                              OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                          H     CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                  CF.sub.3      H     H        CH.sub.3                                                                              CH.sub.3                                   CF.sub.3      H     H        OCH.sub.3                                                                             OCH.sub.3                                  CF.sub.3      H     CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                  N(CH.sub.3).sub.2                                                                            H     H        CH.sub.3                                                                              OCH.sub.3                                  N(CH.sub.3).sub.2                                                                            H     H        OCH.sub.3                                                                             OCH.sub.3                                  N(CH.sub.3).sub.2                                                                            H     CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                  N(CH.sub.3)CH.sub.2 CH.sub.3                                                                 H     H        CH.sub.3                                                                              OCH.sub.3                                  N(CH.sub.2 CH.sub.3).sub.2                                                                   H     H        OCH.sub.3                                                                             OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                            H     H        CH.sub.3                                                                              OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                            H     H        OCH.sub.3                                                                             OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                            H     CH.sub.3 CH.sub.3                                                                              CH.sub.3                                   CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                                H     H        CH.sub.3                                                                              OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                   H     H        OCH.sub.3                                                                             OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                                   H     CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                  C.sub.6 H.sub.5                                                                              H     H        CH.sub.3                                                                              CH.sub.3                                   C.sub.6 H.sub.5                                                                              H     H        CH.sub.3                                                                              OCH.sub.3                                  C.sub.6 H.sub.5                                                                              H     H        OCH.sub.3                                                                             OCH.sub.3                                  C.sub.6 H.sub.5                                                                              H     CH.sub.3 OCH.sub.3                                                                             OCH.sub.3                                  2'-C.sub.6 H.sub.4 Cl                                                                        H     H        CH.sub.3                                                                              OCH.sub.3                                  2'-C.sub.6 H.sub.4 CH.sub.3                                                                  H     H        OCH.sub.3                                                                             OCH.sub.3                                  2'-C.sub.6 H.sub.4 OCH.sub.3                                                                 H     H        OCF.sub.2 H                                                                           OCH.sub.3                                  3'-C.sub.6 H.sub.4 Br                                                                        H     H        CH.sub.3                                                                              OCH.sub.3                                  4'-C.sub.6 H.sub.4 F                                                                         H     H        Cl     OCH.sub.3.sup.b,d                          CH.sub.2 CO.sub.2 CH.sub.3                                                                   H     H        CH.sub.3                                                                              OCH.sub.3                                  CH.sub. 2 CO.sub.2 CH.sub.3                                                                  H     H        OCH.sub.3                                                                             OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                                   H     CH.sub.3 Cl     OCH.sub.3.sup.b,d                           ##STR94##    H     H        OCH.sub.3                                                                             OCF.sub.2 H                                OSO.sub.2 CH.sub.3                                                                           H     H        CH.sub.3                                                                              OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                           H     H        OCH.sub.3                                                                             OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                           H     CH.sub.3 Cl     OCH.sub.3.sup.b,d                          OSO.sub.2 CH.sub.3                                                                           H     CH.sub.3 OCH.sub.3                                                                             OCF.sub.2 H                                OSO.sub.2 CF.sub.3                                                                           H     H        CH.sub.3                                                                              OCH.sub.3                                  CH.sub.2 OCH.sub.3                                                                           H     H        CH.sub.3                                                                              OCH.sub.3                                  CH.sub.2 OCH.sub.3                                                                           H     H        OCH.sub.3                                                                             OCH.sub.3                                  CH.sub.2 OCH.sub.3                                                                           H     CH.sub.3 OCH.sub.3                                                                             OCF.sub.2 H                                CH.sub.2 OCH.sub.3                                                                           H     CH.sub.3 CH.sub.3                                                                              CH.sub.3                                   CH.sub.2 OCF.sub.2 H                                                                         H     H        OCH.sub.3                                                                             OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                         H     OCH.sub.3                                                                               OCF.sub.2 H                                       CH.sub.2 OCF.sub.2 H                                                                         H     CH.sub.3 Cl     OCH.sub.3.sup.b,d                          CH.sub.2 OCF.sub.2 H                                                                         H     CH.sub.3 CH.sub.3                                                                              OCH.sub.3                                  ______________________________________                                          .sup.a Z = N                                                                   .sup.b Z = CH                                                                  ##STR95##                                                                      .sup.c Z = N                                                                   .sup.d Z = CH                                                                  ##STR96##                                                                

                  TABLE 8                                                          ______________________________________                                         (a.) Z = N (b.) Z = CH                                                                     ##STR97##                                                          (c.) Z = N (d.) Z = CH                                                                     ##STR98##                                                          (e.) Z = N (f.) Z = CH                                                                     ##STR99##                                                          R.sub.1    R.sub.3                                                                               W       R.sub.15                                                                            R.sub.16                                                                            X     Y                                    ______________________________________                                         SCH.sub.3  H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H      O       H    H    OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H      O       CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H      O       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H      O       CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                             SCH.sub.2 CH.sub.3                                                                        H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.2 CH.sub.2 CH.sub.3                                                               H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H      O       H    H    CH.sub.3                                                                             CH.sub.3                             S(O)CH.sub.3                                                                              H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H      O       CH.sub.3                                                                            H    Cl    OCH.sub.3.sup.b,d,f                  S(O)CH.sub.3                                                                              H      O       H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      O       H    H    OCH.sub.3                                                                            OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      O       CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      O       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H      O       H    H    CH.sub.3                                                                             CH.sub.3                             CF.sub.3   H      O       CH.sub.3                                                                            H    OCH.sub.3                                                                            CH.sub.3                             CF.sub.3   H      O       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H      O       CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      O       H    H    OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      O       CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      O       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.2 CH.sub.3).sub.2                                                                H      O       H    H    OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      O       CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      O       H    CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                             CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                                H      O       H    H    OCH.sub.3                                                                            OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                                H      O       CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      O       H    H    CH.sub.3                                                                             CH.sub.3                             C.sub.6 H.sub.5                                                                           H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      O       H    H    OCH.sub.3                                                                            OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      O       CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      O       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      O       CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                          2'-C.sub.6 H.sub.4 Cl                                                                     H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H      O       H    H    OCH.sub.3                                                                            OCH.sub.3                            2'-C.sub.6 H.sub.4 CH.sub.3                                                               H      O       H    H    Cl    OCH.sub.3.sup. b,d,f                 3'-C.sub.6 H.sub.4 Br                                                                     H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            4'-C.sub.6 H.sub.4 F                                                                      H      O       H    H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      O       CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      O       H    CH.sub.3                                                                            Cl    OCH.sub.3.sup.b,d,f                   ##STR100##                                                                               H      O       H    H    OCH.sub.3                                                                            OCF.sub.2 H                          OSO.sub.2 CH.sub.3                                                                        H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                        H      O       CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                        H      O       H    CH.sub.3                                                                            Cl    OCH.sub.3.sup.b,d,f                  OSO.sub.2 CH.sub.3                                                                        H      O       CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                          OSO.sub.2 CF.sub.3                                                                        H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      O       H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      O       CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      O       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCH.sub.3                                                                        H      O       CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                             CH.sub.2 OCF.sub.2 H                                                                      H      O       H    H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                      H      O       CH.sub.3                                                                            H    OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCF.sub.2 H                                                                      H      O       H    CH.sub.3                                                                            Cl    OCH.sub.3.sup.b,d,f                  CH.sub.2 OCF.sub.2 H                                                                      H      O       CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H      NCH.sub.3                                                                              H    H    OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H      NCH.sub.3                                                                              CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H      NCH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H      NH      CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                             SCH.sub.2 CH.sub.3                                                                        H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.2 CH.sub.2 CH.sub.3                                                               H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H      NH      H    H    CH.sub.3                                                                             CH.sub.3                             S(O)CH.sub.3                                                                              H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H      NCH.sub.3                                                                              CH.sub.3                                                                            H    Cl    OCH.sub.3.sup.b,d,f                  S(O)CH.sub.3                                                                              H      NCH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      NCH.sub. 3                                                                             H    H    OCH.sub.3                                                                            OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      NCH.sub.3                                                                              CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      NCH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H      NH      H    H    CH.sub.3                                                                             CH.sub.3                             CF.sub.3   H      NCH.sub.3                                                                              CH.sub.3                                                                            H    OCH.sub.3                                                                            CH.sub.3                             CF.sub.3   H      NCH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H      NH      CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      NCH.sub.3                                                                              H    H    OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      NCH.sub.3                                                                              CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      NCH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.2 CH.sub.3).sub.2                                                                H      NCH.sub.3                                                                              H    H    OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      NCH.sub.3                                                                              CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      NCH.sub.3                                                                              H    CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                             CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                                H      NCH.sub.3                                                                              H    H    OCH.sub.3                                                                            OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                                H      NH      CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             CH.sub.3                             C.sub.6 H.sub.5                                                                           H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      NCH.sub.3                                                                              H    H    OCH.sub.3                                                                            OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      NCH.sub.3                                                                              CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      NCH.sub.3                                                                              H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      NCH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                          2'-C.sub.6 H.sub.4 Cl                                                                     H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H      NCH.sub.3                                                                              H    H    OCH.sub.3                                                                            OCH.sub.3                            2'-C.sub.6 H.sub.4 CH.sub.3                                                               H      NCH.sub.3                                                                              H    H    Cl    OCH.sub.3.sup.b,d,f                  3'-C.sub.6 H.sub.4 Br                                                                     H      NH      H    H    CH.sub.3                                                                             OCH.sub.3                            4'-C.sub.6 H.sub. 4 F                                                                     H      NCH.sub.3                                                                              H    H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      NCH.sub.3                                                                              CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      NCH.sub.3                                                                              H    CH.sub.3                                                                            Cl    OCH.sub.3.sup.b,d,f                   ##STR101##                                                                               H      NCH.sub.3                                                                              H    H    OCH.sub.3                                                                            OCF.sub.2 H                          OSO.sub.2 CH.sub.3                                                                        H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                        H      NCH.sub.3                                                                              CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                        H      NCH.sub.3                                                                              H    CH.sub.3                                                                            Cl    OCH.sub.3.sup.b,d,f                  OSO.sub.2 CH.sub.3                                                                        H      NCH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                          OSO.sub.2 CF.sub.3                                                                        H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      NCH.sub.3                                                                              H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      NCH.sub.3                                                                              CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      NH      H    CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCH.sub.3                                                                        H      NCH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                             CH.sub.2 OCF.sub.2 H                                                                      H      NCH.sub.3                                                                              H    H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                      H      NCH.sub.3                                                                              CH.sub.3                                                                            H    OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCF.sub.2 H                                                                      H      NCH.sub.3                                                                              H    CH.sub.3                                                                            Cl    OCH.sub.3.sup.b,d,f                  CH.sub.2 OCF.sub.2 H                                                                      H      NCH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H      S       H    H    OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H      S       CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H      S       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H      S       CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                             SCH.sub.3  3-Cl   S       CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            SCH.sub.2 CH.sub.3                                                                        H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            SCH.sub.2 CH.sub.2 CH.sub.3                                                               H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H      S       H    H    CH.sub.3                                                                             CH.sub.3                             S(O)CH.sub.3                                                                              H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H      S       CH.sub.3                                                                            H    Cl    OCH.sub.3.sup.b,d,f                  S(O)CH.sub.3                                                                              H      S       H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      S       H    H    OCH.sub.3                                                                            OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      S       CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H      S       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H      S       H    H    CH.sub.3                                                                             CH.sub.3                             CF.sub.3   H      S       CH.sub.3                                                                            H    OCH.sub.3                                                                            CH.sub.3                             CF.sub.3   H      O       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H      S       CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      S       H    H    OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      S       CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H      S       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.2 CH.sub.3).sub.2                                                                H      S       H    H    OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      S       CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H      S       H    CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                             CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                                H      S       H    H    OCH.sub.3                                                                            OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                                H      S       CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      S       H    H    CH.sub.3                                                                             CH.sub.3                             C.sub.6 H.sub.5                                                                           H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      S       H    H    OCH.sub.3                                                                            OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      S       CH.sub.3                                                                            H    CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      S       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            C.sub.6 H.sub.5                                                                           H      S       CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                          2'-C.sub.6 H.sub.4 Cl                                                                     H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H      S       H    H    OCH.sub.3                                                                            OCH.sub.3                            2'-C.sub.6 H.sub.4 CH.sub.3                                                               H      S       H    H    Cl    OCH.sub.3.sup.b,d,f                  3'-C.sub.6 H.sub.4 Br                                                                     H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            4'-C.sub.6 H.sub.4 F                                                                      H      S       H    H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      S       CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H      S       H    CH.sub.3                                                                            Cl    OCH.sub.3.sup.b,d,f                   ##STR102##                                                                               H      S       H    H    OCH.sub.3                                                                            OCF.sub.2 H                          OSO.sub.2 CH.sub.3                                                                        H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                        H      S       CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                        H      S       H    CH.sub.3                                                                            Cl    OCH.sub.3.sup.b,d,f                  OSO.sub.2 CH.sub.3                                                                        H      S       CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                          OSO.sub.2 CF.sub.3                                                                        H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      S       H    H    CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      S       CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H      S       H    CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCH.sub.3                                                                        H      S       CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                             CH.sub.2 OCF.sub.2 H                                                                      H      S       H    H    OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                      H      S       CH.sub.3                                                                            H    OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCF.sub.2 H                                                                      H      S       H    CH.sub. 3                                                                           Cl    OCH.sub.3.sup.b,d,f                  CH.sub.2 OCF.sub.2 H                                                                      H      S       CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            ______________________________________                                    

                  TABLE 9                                                          ______________________________________                                         (a.) Z = N (b.) Z = CH                                                                     ##STR103##                                                         (c.) Z = N (d.) Z = CH                                                                     ##STR104##                                                         (e.) Z = N (f.) Z = CH                                                                     ##STR105##                                                         R.sub.1     R.sub.3                                                                              R.sub.19                                                                               R.sub.20                                                                              X      Y                                      ______________________________________                                         SCH.sub.3   H     H       H      CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3   H     H       H      OCH.sub.3                                                                             OCH.sub.3                              SCH.sub.3   H     3-CH.sub.3                                                                             H      CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3   H     4-CH.sub.3                                                                             H      CH.sub.3                                                                              CH.sub.3                               SCH.sub.2 CH.sub.3                                                                         H     H       H      CH.sub.3                                                                              OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub.3                                                                H     H       H      CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                               H     H       H      CH.sub.3                                                                              CH.sub.3                               S(O)CH.sub.3                                                                               H     H       H      CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                               H     5-CH.sub.3                                                                             H      Cl.sup.b,d,f                                                                          OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                        H     H       H      OCH.sub.3                                                                             OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                        H     H       H      CH.sub.3                                                                              OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                        H     6-CH.sub.3                                                                             H      OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3    H     H       H      CH.sub.3                                                                              CH.sub.3                               CF.sub.3    H     H       H      OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3    H     3-CH.sub.3                                                                             4-CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                          H     H       H      CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                          H     H       H      OCH.sub.3                                                                             OCH.sub.3                              N(CH.sub.3).sub.2                                                                          H     3-CH.sub.3                                                                             5-CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3)CH.sub.2 CH.sub.3                                                               H     H       H      CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.2 CH.sub.3).sub.2                                                                 H     H       H      OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                          H     H       H      CH.sub.3                                                                              OCH.sub.3                              CO.sub.2 CH.sub.3                                                                          H     H       H      OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                          H     3-CH.sub.3                                                                             6-CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                              H     H       H      CH.sub.3                                                                              OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                                 H     H       H      OCH.sub.3                                                                             OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                                 H     4-CH.sub.3                                                                             5-CH.sub. 3                                                                           CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                            H     H       H      CH.sub.3                                                                              CH.sub.3                               C.sub.6 H.sub.5                                                                            H     H       H      CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                            H     H       H      OCH.sub.3                                                                             OCH.sub.3                              C.sub.6 H.sub.5                                                                            H     4-CH.sub.3                                                                             6-CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 Cl                                                                      H     H       H      CH.sub.3                                                                              OCH.sub.3                              2'-C.sub.6 H.sub.4 CH.sub.3                                                                H     H       H      OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 OCH.sub.3                                                               H     H       H      OCF.sub.2 H                                                                           OCH.sub.3                              3'-C.sub.6 H.sub.4 Br                                                                      H     H       H      CH.sub.3                                                                              OCH.sub.3                              4'-C.sub.6 H.sub.4 F                                                                       H     H       H      Cl.sup.b,d,f                                                                          OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                 H     H       H      CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                 H     H       H      OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                 H     5-CH.sub.3                                                                             6-CH.sub.3                                                                            Cl.sup.b,d,f                                                                          OCH.sub.3                               ##STR106## H     H       H      OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CH.sub.3                                                                         H     H       H      CH.sub.3                                                                              OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                         H     H       H      OCH.sub.3                                                                             OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                         H     6-CH.sub.3                                                                             H      Cl.sup.b,d,f                                                                          OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                         H     3-CH.sub.3                                                                             H      OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CF.sub.3                                                                         H     H       H      CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                         H     H       H      CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                         H     H       H      OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                         H     6-CH.sub.3                                                                             H      OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCH.sub.3                                                                         H     3-CH.sub.3                                                                             H      CH.sub.3                                                                              CH.sub.3                               CH.sub.2 OCF.sub.2 H                                                                       H     H       H      OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                       H     H       H      OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCF.sub.2 H                                                                       H     6-CH.sub.3                                                                             H      Cl.sup.b,d,f                                                                          OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                       H     3-CH.sub.3                                                                             H      CH.sub.3                                                                              OCH.sub.3                              ______________________________________                                    

                  TABLE 10                                                         ______________________________________                                         (a.) Z = N (b.) Z = CH                                                                   ##STR107##                                                           R.sub.1    R.sub.3                                                                              R.sub.21                                                                               R.sub.22                                                                            R.sub.23                                                                             X     Y                                    ______________________________________                                         SCH.sub.3  H     CH.sub.3                                                                               H    OCH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H     CH.sub.3                                                                               CH.sub.3                                                                            H     CH.sub.3                                                                             OCH.sub.3                            SCH.sub.3  H     H       CH.sub.3                                                                            H     OCH.sub.3                                                                            OCH.sub.3                            SCH.sub.3  H     CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                             SCH.sub.2 CH.sub.3                                                                        H     OCH.sub.3                                                                              H    OCH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                            SCH.sub.2 CH.sub.2 CH.sub.3                                                               H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H     CH.sub.3                                                                               H    OCH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                             S(O)CH.sub.3                                                                              H     H       H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H     CH.sub.3                                                                               H    CH.sub.3                                                                             Cl.sup.b                                                                             OCH.sub.3                            S(O)CH.sub.3                                                                              H     H       CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            S(O).sub.2 CH.sub.3                                                                       H     H       CH.sub.3                                                                            H     OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H     OCH.sub.3                                                                              H    CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                             CF.sub.3   H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            CH.sub.3                             CF.sub.3   H     H       CH.sub.3                                                                            H     OCH.sub.3                                                                            OCH.sub.3                            CF.sub.3   H     CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H     H       CH.sub.3                                                                            CH.sub.3                                                                             CH.sub. 3                                                                            OCH.sub.3                            N(CH.sub.3).sub.2                                                                         H     H       CH.sub.3                                                                            H     OCH.sub.3                                                                            OCH.sub.3                            N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            N(CH.sub.2 CH.sub.3).sub.2                                                                H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            CO.sub.2 CH.sub.3                                                                         H     H       CH.sub.3                                                                            H     CH.sub.3                                                                             CH.sub.3                             CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                                H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            SO.sub.2 N(CH.sub.3).sub.2                                                                H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                             C.sub.6 H.sub.5                                                                           H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            C.sub.6 H.sub.5                                                                           H     CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            C.sub.6 H.sub.5                                                                           H     H       CH.sub.3                                                                            H     OCH.sub.3                                                                            OCH.sub.3                            2'-C.sub.6 H.sub.4 Cl                                                                     H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            3'-C.sub.6 H.sub.4 Br                                                                     H     CH.sub.3                                                                               H    OCH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                            4'-C.sub.6 H.sub.4 F                                                                      H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            2'-C.sub.6 H.sub.4 CH.sub.3                                                               H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 CO.sub.2 CH.sub.3                                                                H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 CO.sub.2 CH.sub.3                                                                H     H       CH.sub.3                                                                            CH.sub.3                                                                             Cl.sup.b                                                                             OCH.sub.3                             ##STR108##                                                                               H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCF.sub.2 H                          OSO.sub.2 CH.sub.3                                                                        H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                        H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            OSO.sub.2 CH.sub.3                                                                        H     H       CH.sub.3                                                                            H     Cl.sup.b                                                                             OCH.sub.3                            OSO.sub.2 CH.sub. 3                                                                       H     CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                                                                            OCF.sub.2 H                          OSO.sub.2 CF.sub.3                                                                        H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H     CH.sub.3                                                                               H    CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCH.sub.3                                                                        H     H       CH.sub.3                                                                            H     OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCH.sub.3                                                                        H     CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                             CH.sub.2 OCF.sub.2 H                                                                      H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                      H     CH.sub.3                                                                               H    CH.sub.3                                                                             OCH.sub.3                                                                            OCF.sub.2 H                          CH.sub.2 OCF.sub.2 H                                                                      H     H       CH.sub.3                                                                            H     Cl.sup.b                                                                             OCH.sub.3                            CH.sub.2 OCF.sub.2 H                                                                      H     CH.sub.3                                                                               CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                             OCH.sub.3                            ______________________________________                                    

                  TABLE 11                                                         ______________________________________                                         (a.) Z = N (b.) Z = CH                                                                     ##STR109##                                                         R.sub.1    R.sub.3                                                                               R.sub.24                                                                               R.sub.25                                                                              X      Y                                      ______________________________________                                         SCH.sub.3  H      H       H      CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H      H       H      OCH.sub.3                                                                             OCH.sub.3                              SCH.sub.3  H      3-CH.sub.3                                                                             H      CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H      3-CH.sub.3                                                                             H      CH.sub.3                                                                              CH.sub.3                               SCH.sub.2 CH.sub.3                                                                        H      H       H      CH.sub.3                                                                              OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub.3                                                               H      H       H      CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                              H      H       H      CH.sub.3                                                                              CH.sub.3                               S(O)CH.sub.3                                                                              H      H       H      CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                              H      5-CH.sub.3                                                                             H      Cl.sup.b                                                                              OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                       H      H       H      OCH.sub.3                                                                             OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                       H      H       H      CH.sub.3                                                                              OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                       H      6-CH.sub.3                                                                             H      OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3   H      H       H      CH.sub.3                                                                              CH.sub.3                               CF.sub.3   H      H       H      OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3   H      3-CH.sub.3                                                                             5-CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                         H      H       H      CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                         H      H       H      OCH.sub.3                                                                             OCH.sub.3                              N(CH.sub.3).sub.2                                                                         H      3-CH.sub.3                                                                             6-CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H      H       H      CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.2 CH.sub.3).sub.2                                                                H      H       H      OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                         H      H       H      CH.sub.3                                                                              OCH.sub.3                              CO.sub.2 CH.sub.3                                                                         H      H       H      OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                         H      5-CH.sub.3                                                                             6-CH.sub.3                                                                            CH.sub.3                                                                              CH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             H      H       H      CH.sub.3                                                                              OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                                H      H       H      OCH.sub.3                                                                             OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                                H      3-CH.sub.3                                                                             6-CH.sub.3                                                                            CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                           H      H       H      CH.sub.3                                                                              CH.sub.3                               C.sub.6 H.sub.5                                                                           H      H       H      CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                           H      H       H      OCH.sub.3                                                                             OCH.sub.3                              C.sub.6 H.sub.5                                                                           H      5-CH.sub.3                                                                             6-CH.sub.3                                                                            OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 Cl                                                                     H      H       H      CH.sub.3                                                                              OCH.sub.3                              2'-C.sub.6 H.sub.4 CH.sub.3                                                               H      H       H      OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H      H       H      OCF.sub.2 H                                                                           OCH.sub.3                              3'-C.sub.6 H.sub.4 Br                                                                     H      H       H      CH.sub.3                                                                              OCH.sub.3                              4'-C.sub.6 H.sub.4 F                                                                      H      H       H      Cl.sup.b                                                                              OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                H      H       H      CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                H      H       H      OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                H      3-CH.sub.3                                                                             5-CH.sub.3                                                                            Cl.sup.b                                                                              OCH.sub.3                               ##STR110##                                                                               H      H       H      OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CH.sub.3                                                                        H      H       H      CH.sub.3                                                                              OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                        H      H       H      OCH.sub.3                                                                             OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                        H      6-CH.sub.3                                                                             H      Cl.sup.b                                                                              OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                        H      6-CH.sub.3                                                                             H      OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CF.sub.3                                                                        H      H       H      CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                        H      H       H      CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                        H      H       H      OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                        H      5-CH.sub.3                                                                             H      OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCH.sub.3                                                                        H      6-CH.sub.3                                                                             H      CH.sub.3                                                                              CH.sub.3                               CH.sub.2 OCF.sub.2 H                                                                      H      H       H      OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                      H      H       H      OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCF.sub.2 H                                                                      H      5-CH.sub.3                                                                             H      Cl.sup.b                                                                              OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                      H      6-CH.sub.3                                                                             H      CH.sub.3                                                                              OCH.sub.3                              ______________________________________                                    

                  TABLE 12                                                         ______________________________________                                         (a.) Z = N (b.) Z = CH                                                                   ##STR111##                                                           R.sub.1    R.sub.3                                                                               R.sub.21                                                                               R.sub.23                                                                              X      Y                                      ______________________________________                                         SCH.sub.3  H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H      H       H      OCH.sub.3                                                                             OCH.sub.3                              SCH.sub.3  H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              SCH.sub.3  H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                               SCH.sub.2 CH.sub.3                                                                        H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              SCH.sub.2 CH.sub.2 CH.sub.3                                                               H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                              H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                               S(O)CH.sub.3                                                                              H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              S(O)CH.sub.3                                                                              H      CH.sub.3                                                                               OCH.sub.3                                                                             Cl.sup.b                                                                              OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                       H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                       H      H       CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              S(O).sub.2 CH.sub.3                                                                       H      OCH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3   H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                               CF.sub.3   H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              CF.sub.3   H      OCH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                         H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3).sub.2                                                                         H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              N(CH.sub.3).sub.2                                                                         H      CH.sub.3                                                                               OCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              N(CH.sub.2 CH.sub.3).sub.2                                                                H      H       H      OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                         H      H       OCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                              CO.sub.2 CH.sub.3                                                                         H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              CO.sub.2 CH.sub.3                                                                         H      OCH.sub.3                                                                              OCH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                                H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                                H      OCH.sub.3                                                                              OCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                           H      H       OCH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                               C.sub.6 H.sub.5                                                                           H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              C.sub.6 H.sub.5                                                                           H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              C.sub.6 H.sub.5                                                                           H      CH.sub.3                                                                               OCH.sub.3                                                                             OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 Cl                                                                     H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              2'-C.sub.6 H.sub.4 CH.sub.3                                                               H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              2'-C.sub.6 H.sub.4 OCH.sub.3                                                              H      H       CH.sub.3                                                                              OCF.sub.2 H                                                                           OCH.sub.3                              3'-C.sub.6 H.sub.4 Br                                                                     H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              4'-C.sub.6 H.sub.4 F                                                                      H      CH.sub.3                                                                               CH.sub.3                                                                              Cl.sup.b                                                                              OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                H      OCH.sub.3                                                                              OCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 CO.sub.2 CH.sub.3                                                                H      CH.sub.3                                                                               CH.sub.3                                                                              Cl     OCH.sub.3.sup.b                         ##STR112##                                                                               H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CH.sub.3                                                                        H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                        H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                        H      OCH.sub.3                                                                              H      Cl.sup.b                                                                              OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                        H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCF.sub.2 H                            OSO.sub.2 CF.sub.3                                                                        H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                        H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                        H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCH.sub.3                                                                        H      CH.sub.3                                                                               H      OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCH.sub.3                                                                        H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              CH.sub.3                               CH.sub.2 OCF.sub.2 H                                                                      H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                      H      CH.sub.3                                                                               CH.sub.3                                                                              OCH.sub.3                                                                             OCF.sub.2 H                            CH.sub.2 OCF.sub.2 H                                                                      H      CH.sub.3                                                                               H      Cl.sup.b                                                                              OCH.sub.3                              CH.sub.2 OCF.sub.2 H                                                                      H      CH.sub.3                                                                               CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                              ______________________________________                                    

                  TABLE 13                                                         ______________________________________                                         (a.) Z = N (b.) Z = CH                                                                   ##STR113##                                                           R.sub.1    R.sub.3                                                                              W'    R.sub.26                                                                            R.sub.27                                                                            R.sub.28                                                                            X     Y                                  ______________________________________                                         SCH.sub.3  H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          SCH.sub.3  H     O     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          SCH.sub.3  H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          SCH.sub.3  H     O     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                          SCH.sub.3  H     O     CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                           SCH.sub.2 CH.sub.3                                                                        H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          SCH.sub.2 CH.sub.2 CH.sub.3                                                               H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          S(O)CH.sub.3                                                                              H     O     H    H    H    CH.sub.3                                                                             CH.sub.3                           S(O)CH.sub.3                                                                              H     O     H    H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          S(O)CH.sub.3                                                                              H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            Cl.sup.b                                                                             OCH.sub.3                          S(O)CH.sub.3                                                                              H     O     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          S(O).sub.2 CH.sub.3                                                                       H     O     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          S(O).sub.2 CH.sub.3                                                                       H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          S(O).sub.2 CH.sub.3                                                                       H     O     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                          CF.sub.3   H     O     H    H    H    CH.sub.3                                                                             CH.sub.3                           CF.sub.3   H     O     CH.sub.3                                                                            H    H    OCH.sub.3                                                                            CH.sub.3                           CF.sub.3   H     O     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                          CF.sub.3   H     O     CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          N(CH.sub.3).sub.2                                                                         H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          N(CH.sub.3).sub.2                                                                         H     O     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          N(CH.sub.3).sub.2                                                                         H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          N(CH.sub.3).sub.2                                                                         H     O     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                          N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          N(CH.sub.2 CH.sub.3).sub.2                                                                H     O     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          CO.sub.2 CH.sub.3                                                                         H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          CO.sub.2 CH.sub.3                                                                         H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                          CO.sub.2 CH.sub.3                                                                         H     O     H    CH.sub.3                                                                            H    CH.sub.3                                                                             CH.sub.3                           CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          SO.sub.2 N(CH.sub.3).sub.2                                                                H     O     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          SO.sub.2 N(CH.sub.3).sub.2                                                                H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          C.sub.6 H.sub.5                                                                           H     O     H    H    H    CH.sub.3                                                                             CH.sub.3                           C.sub.6 H.sub.5                                                                           H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          C.sub.6 H.sub.5                                                                           H     O     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          C.sub.6 H.sub.5                                                                           H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          C.sub.6 H.sub.5                                                                           H     O     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                          2'-C.sub.6 H.sub.4 Cl                                                                     H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          2'-C.sub.6 H.sub.4 Br                                                                     H     O     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          2'-C.sub.6 H.sub.4 F                                                                      H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          3'-C.sub.6 H.sub.4 CH.sub.3                                                               H     O     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          4'-C.sub.6 H.sub.4 OCH.sub.3                                                              H     O     H    H    H    OCH.sub.3                                                                            OCF.sub.2 H                        CH.sub.2 CO.sub.2 CH.sub.3                                                                H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          CH.sub.2 CO.sub.2 CH.sub.3                                                                H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                          CH.sub.2 CO.sub.2 CH.sub.3                                                                H     O     H    CH.sub.3                                                                            CH.sub.3                                                                            Cl.sup.b                                                                             OCH.sub.3                           ##STR114##                                                                               H     O     H    H    H    OCH.sub.3                                                                            OCF.sub.2 H                        OSO.sub.2 CH.sub.3                                                                        H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          OSO.sub.2 CH.sub.3                                                                        H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                          OSO.sub.2 CH.sub.3                                                                        H     O     H    CH.sub.3                                                                            H    Cl.sup.b                                                                             OCH.sub.3                          OSO.sub.2 CH.sub.3                                                                        H     O     CH.sub. 3                                                                           CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                        OSO.sub.2 CF.sub.3                                                                        H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          CH.sub.2 OCH.sub.3                                                                        H     O     H    H    H    CH.sub.3                                                                             OCH.sub.3                          CH.sub.2 OCH.sub.3                                                                        H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                          CH.sub.2 OCH.sub.3                                                                        H     O     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCF.sub.2 H                        CH.sub.2 OCH.sub.3                                                                        H     O     CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                           CH.sub.2 OCF.sub.2 H                                                                      H     O     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          CH.sub.2 OCF.sub.2 H                                                                      H     O     CH.sub.3                                                                            H    CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                        CH.sub.2 OCF.sub.2 H                                                                      H     O     H    CH.sub.3                                                                            H    Cl.sup.b                                                                             OCH.sub.3                          CH.sub.2 OCF.sub.2 H                                                                      H     O     CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          SCH.sub.3  H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          SCH.sub.3  H     S     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          SCH.sub.3  H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          SCH.sub.3  H     S     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                          SCH.sub.3  H     S     CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                           SCH.sub.2 CH.sub.3                                                                        H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          SCH.sub.2 CH.sub.2 CH.sub.3                                                               H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          S(O)CH.sub.3                                                                              H     S     H    H    H    CH.sub.3                                                                             CH.sub.3                           S(O)CH.sub.3                                                                              H     S     H    H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          S(O)CH.sub.3                                                                              H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            Cl.sup.b                                                                             OCH.sub.3                          S(O)CH.sub.3                                                                              H     S     H    CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          S(O).sub.2 CH.sub.3                                                                       H     S     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          S(O).sub.2 CH.sub.3                                                                       H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          S(O).sub.2 CH.sub.3                                                                       H     S     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                          CF.sub.3   H     S     H    H    H    CH.sub.3                                                                             CH.sub.3                           CF.sub.3   H     S     CH.sub.3                                                                            H    H    OCH.sub.3                                                                            CH.sub.3                           CF.sub.3   H     S     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                          CF.sub.3   H     S     CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          N(CH.sub.3).sub.2                                                                         H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          N(CH.sub.3).sub.2                                                                         H     S     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          N(CH.sub.3).sub.2                                                                         H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          N(CH.sub.3).sub.2                                                                         H     S     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                          N(CH.sub.3)CH.sub.2 CH.sub.3                                                              H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          N(CH.sub.2 CH.sub.3).sub.2                                                                H     S     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          CO.sub.2 CH.sub.3                                                                         H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          CO.sub.2 CH.sub.3                                                                         H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                          CO.sub.2 CH.sub.3                                                                         H     S     H    CH.sub.3                                                                            H    CH.sub.3                                                                             CH.sub.3                           CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          SO.sub.2 N(CH.sub.3).sub.2                                                                H     S     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          SO.sub.2 N(CH.sub.3).sub.2                                                                H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          C.sub.6 H.sub.5                                                                           H     S     H    H    H    CH.sub.3                                                                             CH.sub.3                           C.sub.6 H.sub.5                                                                           H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          C.sub.6 H.sub.5                                                                           H     S     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          C.sub.6 H.sub.5                                                                           H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            CH.sub. 3                                                                            OCH.sub.3                          C.sub.6 H.sub.5                                                                           H     S     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCH.sub.3                          2'-C.sub.6 H.sub.4 Cl                                                                     H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          2'-C.sub.6 H.sub.4 Br                                                                     H     S     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          2'-C.sub.6 H.sub.4 F                                                                      H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          3'-C.sub.6 H.sub.4 CH.sub.3                                                               H     S     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          4'-C.sub.6 H.sub.4 OCH.sub.3                                                              H     S     H    H    H    OCH.sub.3                                                                            OCF.sub.2 H                        CH.sub.2 CO.sub.2 CH.sub.3                                                                H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          CH.sub.2 CO.sub.2 CH.sub.3                                                                H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                          CH.sub.2 CO.sub.2 CH.sub.3                                                                H     S     H    CH.sub.3                                                                            CH.sub.3                                                                            Cl.sup.b                                                                             OCH.sub.3                           ##STR115##                                                                               H     S     H    H    H    OCH.sub.3                                                                            OCF.sub.2 H                        OSO.sub.2 CH.sub.3                                                                        H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          OSO.sub.2 CH.sub.3                                                                        H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                          OSO.sub.2 CH.sub.3                                                                        H     S     H    CH.sub.3                                                                            H    Cl.sup.b                                                                             OCH.sub.3                          OSO.sub.2 CH.sub.3                                                                        H     S     CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                        OSO.sub.2 CH.sub.3                                                                        H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          CH.sub.2 OCH.sub.3                                                                        H     S     H    H    H    CH.sub.3                                                                             OCH.sub.3                          CH.sub.2 OCH.sub.3                                                                        H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            OCH.sub.3                                                                            OCH.sub.3                          CH.sub.2 OCH.sub.3                                                                        H     S     H    CH.sub.3                                                                            H    OCH.sub.3                                                                            OCF.sub.2 H                        CH.sub.2 OCH.sub.3                                                                        H     S     CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                           CH.sub.2 OCF.sub.2 H                                                                      H     S     H    H    H    OCH.sub.3                                                                            OCH.sub.3                          CH.sub.2 OCF.sub.2 H                                                                      H     S     CH.sub.3                                                                            H    CH.sub.3                                                                            OCH.sub.3                                                                            OCF.sub.2 H                        CH.sub.2 OCF.sub.2 H                                                                      H     S     H    CH.sub.3                                                                            H    Cl.sup.b                                                                             OCH.sub.3                          CH.sub.2 OCF.sub.2 H                                                                      H     S     CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                             OCH.sub.3                          ______________________________________                                    

                                      TABLE 14                                     __________________________________________________________________________     (a.) Z = N (b.) Z = CH                                                                     ##STR116##                                                         R.sub.1  R.sub.3                                                                          W'                                                                               R.sub.26                                                                          R.sub.27                                                                          R.sub.28                                                                          R.sub.29                                                                          R.sub.30                                                                          R.sub.31                                                                          X    Y                                          __________________________________________________________________________     SCH.sub.3                                                                               H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3                                                                               H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  SCH.sub.3                                                                               H O CH.sub.3                                                                          H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  SCH.sub. 3                                                                              H O H  H  CH.sub.3                                                                          H  H  H  Cl.sup.b                                                                            OCH.sub.3                                  SCH.sub.3                                                                               H O H  H  H  H  CH.sub.3                                                                          H  CH.sub.3                                                                            CH.sub.3                                   SCH.sub.2 CH.sub.3                                                                      H O CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.2 CH.sub.2 CH.sub.3                                                             H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  S(O)CH.sub.3                                                                            H O CH.sub.3                                                                          H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  CH.sub.3                                                                            OCH.sub.3                                  S(O)CH.sub.3                                                                            H O CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                          H  OCH.sub.3                                                                           OCH.sub.3                                  S(O)CH.sub.3                                                                            H O H  H  H  H  H  H  Cl.sup.b                                                                            OCH.sub.3                                  S(O)CH.sub.3                                                                            H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                     H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                     H O CH.sub.3                                                                          CH.sub.3                                                                          H  H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                     H O H  H  CH.sub.3                                                                          CH.sub.3                                                                          H  H  OCH.sub.3                                                                           OCH.sub.3                                  CF.sub.3 H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  CF.sub.3 H O CH.sub.3                                                                          H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  CF.sub.3 H O H  H  CH.sub.3                                                                          H  H  H  Cl.sup.b                                                                            OCH.sub.3                                  CF.sub.3 H O H  H  H  H  CH.sub.3                                                                          H  CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                       H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                       H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                       H O H  H  H  H  H  H  Cl.sup.b                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                       H O CH.sub.3                                                                          H  H  H  H  CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3)CH.sub.2 CH.sub.3                                                            H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.2 CH.sub.3).sub.2                                                              H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                       H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                       H O H  H  CH.sub.3                                                                          H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                       H O H  H  CH.sub.3                                                                          CH.sub.3                                                                          H  H  CH.sub.3                                                                            CH.sub.3                                   CO.sub.2 CH.sub.2 CH.sub. 2 Cl                                                          H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                              H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                              H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                         H O H  H  H  H  H  H  CH.sub.3                                                                            CH.sub.3                                   C.sub.6 H.sub.5                                                                         H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                         H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  C.sub.6 H.sub.5                                                                         H O CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                         H O CH.sub.3                                                                          H  H  H  CH.sub.3                                                                          H  OCH.sub.3                                                                           OCH.sub.3                                  2'-C.sub.6 H.sub.4 Cl                                                                   H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  2'-C.sub.6 H.sub.4 Br                                                                   H O CH.sub.3                                                                          H  CH.sub.3                                                                          H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  2'-C.sub.6 H.sub.4 F                                                                    H O H  H  H  H  H  CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                  3'-C.sub.6 H.sub.4 CH.sub.3                                                             H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  4'-C.sub.6 H.sub.4 OCH.sub.3                                                            H O H  H  H  H  H  H  OCF.sub.2 H                                                                         OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                              H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                              H O H  H  CH.sub.3                                                                          CH.sub.3                                                                          H  H  OCH.sub.3                                                                           OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                              H O H  H  H  H  H  H  Cl.sup.b                                                                            OCH.sub.3                                   ##STR117##                                                                             H O H  H  H  H  H  H  OCF.sub.2 H                                                                         OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                      H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                      H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                      H O H  H  H  H  H  H  Cl.sup.b                                                                            OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                      H O H  H  H  H  H  H  OCF.sub.2 H                                                                         OCH.sub.3                                  OSO.sub.2 CF.sub.3                                                                      H O H  H  H  H  H  CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 OCH.sub.3                                                                      H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 OCH.sub.3                                                                      H O H  H  H  H  H  H  CH.sub.3                                                                            CH.sub.3                                   CH.sub.2 OCH.sub.3                                                                      H O H  H  CH.sub.3                                                                          H  H  H  OCF.sub.2 H                                                                         OCH.sub.3                                  CH.sub.2 OCH.sub.3                                                                      H O H  H  CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                            CH.sub.3                                   CH.sub.2 OCF.sub.2 H                                                                    H O H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                    H O H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                    H O CH.sub.3                                                                          H  H  H  CH.sub.3                                                                          H  Cl.sup.b                                                                            OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                    H O CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3                                                                               H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.3                                                                               H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  SCH.sub.3                                                                               H S CH.sub.3                                                                          H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  SCH.sub.3                                                                               H S H  H  CH.sub.3                                                                          H  H  H  Cl.sup.b                                                                            OCH.sub.3                                  SCH.sub.3                                                                               H S H  H  H  H  CH.sub.3                                                                          H  CH.sub.3                                                                            CH.sub.3                                   SCH.sub.2 CH.sub.3                                                                      H S CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                            OCH.sub.3                                  SCH.sub.2 CH.sub.2 CH.sub.3                                                             H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  S(O)CH.sub.3                                                                            H S CH.sub.3                                                                          H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  CH.sub.3                                                                            OCH.sub.3                                  S(O)CH.sub.3                                                                            H S CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                          H  OCH.sub.3                                                                           OCH.sub.3                                  S(O)CH.sub.3                                                                            H S H  H  H  H  H  H  Cl.sup.b                                                                            OCH.sub.3                                  S(O)CH.sub.3                                                                            H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                     H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                     H S CH.sub.3                                                                          CH.sub.3                                                                          H  H  CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                  S(O).sub.2 CH.sub.3                                                                     H S H  H  CH.sub.3                                                                          CH.sub.3                                                                          H  H  OCH.sub.3                                                                           OCH.sub.3                                  CF.sub.3 H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  CF.sub.3 H S CH.sub.3                                                                          H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  CF.sub.3 H S H  H  CH.sub.3                                                                          H  H  H  Cl.sup.b                                                                            OCH.sub.3                                  CF.sub.3 H S H  H  H  H  CH.sub.3                                                                          H  CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                       H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                       H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3).sub.2                                                                       H S H  H  H  H  H  H  Cl.sup.b                                                                            OCH.sub.3                                  N(CH.sub.3).sub.2                                                                       H S CH.sub.3                                                                          H  H  H  H  CH.sub.3                                                                          OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.3)CH.sub.2 CH.sub.3                                                            H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  N(CH.sub.2 CH.sub.3).sub.2                                                              H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                       H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                       H S H  H  CH.sub.3                                                                          H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                       H S H  H  CH.sub.3                                                                          CH.sub.3                                                                          H  H  CH.sub.3                                                                            CH.sub.3                                   CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                           H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                              H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  SO.sub.2 N(CH.sub.3).sub.2                                                              H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                         H S H  H  H  H  H  H  CH.sub.3                                                                            CH.sub.3                                   C.sub.6 H.sub.5                                                                         H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                         H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  C.sub.6 H.sub.5                                                                         H S CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                            OCH.sub.3                                  C.sub.6 H.sub.5                                                                         H S CH.sub.3                                                                          H  H  H  CH.sub.3                                                                          H  OCH.sub.3                                                                           OCH.sub.3                                  2'-C.sub.6 H.sub.4 Cl                                                                   H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  2'-C.sub.6 H.sub.4 Br                                                                   H S CH.sub.3                                                                          H  CH.sub.3                                                                          H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  2'-C.sub.6 H.sub.4 F                                                                    H S H  H  H  H  H  CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                  3'-C.sub.6 H.sub.4 CH.sub.3                                                             H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  4'-C.sub.6 H.sub.4 OCH.sub.3                                                            H S H  H  H  H  H  H  OCF.sub.2 H                                                                         OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                              H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                              H S H  H  CH.sub.3                                                                          CH.sub.3                                                                          H  H  OCH.sub.3                                                                           OCH.sub.3                                  CH.sub.2 CO.sub.2 CH.sub.3                                                              H S H  H  H  H  H  H  Cl.sup.b                                                                            OCH.sub.3                                   ##STR118##                                                                             H S H  H  H  H  H  H  OCF.sub.2 H                                                                         OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                      H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                      H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                      H S H  H  H  H  H  H  Cl.sup.b                                                                            OCH.sub.3                                  OSO.sub.2 CH.sub.3                                                                      H S H  H  H  H  H  H  OCF.sub.2 H                                                                         OCH.sub.3                                  OSO.sub.2 CF.sub.3                                                                      H S H  H  H  H  H  CH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 OCH.sub.3                                                                      H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 OCH.sub.3                                                                      H S H  H  H  H  H  H  CH.sub.3                                                                            CH.sub.3                                   CH.sub.2 OCH.sub.3                                                                      H S H  H  CH.sub.3                                                                          H  H  H  OCF.sub.2 H                                                                         OCH.sub.3                                  CH.sub.2 OCH.sub.3                                                                      H S H  H  CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                            CH.sub.3                                   CH.sub.2 OCF.sub.2 H                                                                    H S H  H  H  H  H  H  CH.sub.3                                                                            OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                    H S H  H  H  H  H  H  OCH.sub.3                                                                           OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                    H S CH.sub.3                                                                          H  H  H  CH.sub.3                                                                          H  Cl.sup.b                                                                            OCH.sub.3                                  CH.sub.2 OCF.sub.2 H                                                                    H S CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  CH.sub.3                                                                          H  CH.sub.3                                                                            OCH.sub.3                                  __________________________________________________________________________

                  TABLE 15                                                         ______________________________________                                         (a.) Z = N (b.) Z = CH                                                                   ##STR119##                                                           In the following table, R.sub.15 -R.sub.31 are H.                              Q         Q'       R.sub.3 X        Y                                          ______________________________________                                         Q-1       Q-1      H       CH.sub.3 CH.sub.3                                   Q-1       Q-2      H       CH.sub.3 OCH.sub.3                                  Q-1       Q-3      H       OCH.sub.3                                                                               OCH.sub.3                                  Q-1       Q-4      H       Cl.sup.b OCH.sub.3                                  Q-1       Q-5      H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-1       Q-6      H       CH.sub.3 CH.sub.3                                   Q-1       Q-7      H       CH.sub.3 OCH.sub.3                                  Q-1       Q-8      H       OCH.sub.3                                                                               OCH.sub.3                                  Q-1       Q-9      H       Cl.sup.b OCH.sub.3                                  Q-1       Q-10     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-1       Q-11     H       CH.sub.3 CH.sub.3                                   Q-1       Q-12     H       CH.sub.3 OCH.sub.3                                  Q-1       Q-13     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-1       Q-14     H       Cl.sup.b OCH.sub.3                                  Q-1       Q-15     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-1       Q-16     H       CH.sub.3 CH.sub.3                                   Q-1       Q-17     H       CH.sub.3 OCH.sub.3                                  Q-1       Q-18     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-1       Q-19     H       Cl.sup.b OCH.sub.3                                  Q-1       Q-20     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-2       Q-2      H       CH.sub.3 CH.sub.3                                   Q-2       Q-3      H       CH.sub.3 OCH.sub.3                                  Q-2       Q-4      H       OCH.sub.3                                                                               OCH.sub.3                                  Q-2       Q-5      H       Cl.sup.b OCH.sub.3                                  Q-2       Q-6      H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-2       Q-7      H       CH.sub.3 CH.sub.3                                   Q-2       Q-8      H       CH.sub.3 OCH.sub.3                                  Q-2       Q-9      H       OCH.sub.3                                                                               OCH.sub.3                                  Q-2       Q-10     H       Cl.sup.b OCH.sub.3                                  Q-2       Q-11     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-2       Q-12     H       CH.sub.3 CH.sub.3                                   Q-2       Q-13     H       CH.sub.3 OCH.sub.3                                  Q-2       Q-14     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-2       Q-15     H       Cl.sup.b OCH.sub.3                                  Q-2       Q-16     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-2       Q-17     H       CH.sub.3 CH.sub.3                                   Q-2       Q-18     H       CH.sub.3 OCH.sub.3                                  Q-2       Q-19     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-2       Q-20     H       Cl.sup.b OCH.sub.3                                  Q-3       Q-3      H       OCF.sub.2 H                                                                             OCH.sub. 3                                 Q-3       Q-4      H       CH.sub.3 CH.sub.3                                   Q-3       Q-5      H       CH.sub.3 OCH.sub.3                                  Q-3       Q-6      H       OCH.sub.3                                                                               OCH.sub.3                                  Q-3       Q-7      H       Cl.sup.b OCH.sub.3                                  Q-3       Q-8      H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-3       Q-9      H       CH.sub.3 CH.sub.3                                   Q-3       Q-10     H       CH.sub.3 OCH.sub.3                                  Q-3       Q-11     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-3       Q-12     H       Cl.sup.b OCH.sub.3                                  Q-3       Q-13     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-3       Q-14     H       CH.sub.3 CH.sub.3                                   Q-3       Q-15     H       CH.sub.3 OCH.sub.3                                  Q-3       Q-16     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-3       Q-17     H       Cl.sup.b OCH.sub.3                                  Q-3       Q-18     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-3       Q-19     H       CH.sub.3 CH.sub.3                                   Q-3       Q-20     H       CH.sub.3 OCH.sub.3                                  Q-4       Q-4      H       OCH.sub.3                                                                               OCH.sub.3                                  Q-4       Q-5      H       Cl.sup.b OCH.sub.3                                  Q-4       Q-6      H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-4       Q-7      H       CH.sub.3 CH.sub.3                                   Q-4       Q-8      H       CH.sub.3 OCH.sub.3                                  Q-4       Q-9      H       OCH.sub.3                                                                               OCH.sub.3                                  Q-4       Q-10     H       Cl.sup.b OCH.sub.3                                  Q-4       Q-11     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-4       Q-12     H       CH.sub.3 CH.sub.3                                   Q-4       Q-13     H       CH.sub.3 OCH.sub.3                                  Q-4       Q-14     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-4       Q-15     H       Cl.sub.b OCH.sub.3                                  Q-4       Q-16     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-4       Q-17     H       CH.sub.3 CH.sub.3                                   Q-4       Q-18     H       CH.sub.3 OCH.sub.3                                  Q-4       Q-19     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-4       Q-20     H       Cl.sup.b OCH.sub.3                                  Q-5       Q-5      H       CH.sub.3 CH.sub.3                                   Q-5       Q-6      H       CH.sub.3 OCH.sub.3                                  Q-5       Q-7      H       OCH.sub.3                                                                               OCH.sub.3                                  Q-5       Q-8      H       Cl.sup.b OCH.sub.3                                  Q-5       Q-9      H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-5       Q-10     H       CH.sub.3 CH.sub.3                                   Q-5       Q-11     H       CH.sub.3 OCH.sub.3                                  Q-5       Q-12     H       CH.sub.3 OCH.sub.3                                  Q-5       Q-13     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-5       Q-14     H       Cl.sup.b OCH.sub.3                                  Q-5       Q-15     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-5       Q-16     H       CH.sub.3 CH.sub.3                                   Q-5       Q-17     H       CH.sub.3 OCH.sub.3                                  Q-5       Q-18     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-5       Q-19     H       Cl.sup.b OCH.sub.3                                  Q-5       Q-20     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-6       Q-6      H       CH.sub.3 CH.sub.3                                   Q-6       Q-7      H       CH.sub.3 OCH.sub.3                                  Q-6       Q-8      H       OCH.sub.3                                                                               OCH.sub.3                                  Q-6       Q-9      H       Cl.sup.b OCH.sub.3                                  Q-6       Q-10     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-6       Q-11     H       CH.sub. 3                                                                               CH.sub.3                                   Q-6       Q-12     H       CH.sub.3 OCH.sub.3                                  Q-6       Q-13     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-6       Q-14     H       Cl.sup.b OCH.sub.3                                  Q-6       Q-15     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-6       Q-16     H       CH.sub.3 CH.sub.3                                   Q-6       Q-17     H       CH.sub.3 OCH.sub.3                                  Q-6       Q-18     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-6       Q-19     H       Cl.sup.b OCH.sub.3                                  Q-6       Q-20     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-7       Q-7      H       CH.sub.3 CH.sub.3                                   Q-7       Q-8      H       CH.sub.3 OCH.sub.3                                  Q-7       Q-9      H       OCH.sub.3                                                                               OCH.sub.3                                  Q-7       Q-10     H       Cl.sup.b OCH.sub.3                                  Q-7       Q-11     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-7       Q-12     H       CH.sub.3 CH.sub.3                                   Q-7       Q-13     H       CH.sub.3 OCH.sub.3                                  Q-7       Q-14     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-7       Q-15     H       Cl.sup.b OCH.sub.3                                  Q-7       Q-16     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-7       Q-17     H       CH.sub.3 CH.sub.3                                   Q-7       Q-18     H       CH.sub.3 OCH.sub.3                                  Q-7       Q-19     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-7       Q-20     H       Cl.sup.b OCH.sub.3                                  Q-8       Q-8      H       CH.sub.3 CH.sub.3                                   Q-8       Q-9      H       CH.sub.3 OCH.sub.3                                  Q-8       Q-10     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-8       Q-11     H       Cl.sup.b OCH.sub.3                                  Q-8       Q-12     H       OCF.sub. 2 H                                                                            OCH.sub.3                                  Q-8       Q-13     H       CH.sub.3 CH.sub.3                                   Q-8       Q-14     H       CH.sub.3 OCH.sub.3                                  Q-8       Q-15     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-8       Q-16     H       Cl.sup.b OCH.sub.3                                  Q-8       Q-17     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-8       Q-18     H       CH.sub.3 CH.sub.3                                   Q-8       Q-19     H       CH.sub.3 OCH.sub.3                                  Q-8       Q-20     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-9       Q-9      H       Cl.sup.b OCH.sub.3                                  Q-9       Q-10     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-9       Q-11     H       CH.sub.3 CH.sub.3                                   Q-9       Q-12     H       CH.sub.3 OCH.sub.3                                  Q-9       Q-13     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-9       Q-14     H       Cl.sup.b OCH.sub.3                                  Q-9       Q-15     H       CH.sub.3 CH.sub.3                                   Q-9       Q-16     H       CH.sub.3 OCH.sub.3                                  Q-9       Q-17     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-9       Q-18     H       Cl.sup.b OCH.sub.3                                  Q-9       Q-19     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-9       Q-20     H       CH.sub.3 CH.sub.3                                   Q-10      Q-10     H       CH.sub.3 OCH.sub.3                                  Q-10      Q-11     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-10      Q-12     H       Cl.sup.b OCH.sub.3                                  Q-10      Q-13     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-10      Q-14     H       CH.sub.3 CH.sub.3                                   Q-10      Q-15     H       CH.sub.3 OCH.sub.3                                  Q-10      Q-16     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-10      Q-17     H       Cl.sup.b OCH.sub.3                                  Q-10      Q-18     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-10      Q-19     H       CH.sub.3 CH.sub.3                                   Q-10      Q-20     H       CH.sub.3 OCH.sub.3                                  Q-11      Q-11     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-11      Q-12     H       Cl.sup.b OCH.sub.3                                  Q-11      Q-13     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-11      Q-14     H       CH.sub.3 CH.sub.3                                   Q-11      Q-15     H       CH.sub.3 OCH.sub.3                                  Q-11      Q-15     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-11      Q-16     H       Cl.sup.b OCH.sub.3                                  Q-11      Q-17     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-11      Q-18     H       CH.sub.3 CH.sub.3                                   Q-11      Q-19     H       CH.sub.3 OCH.sub.3                                  Q-11      Q-20     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-12      Q-12     H       Cl.sup.b OCH.sub.3                                  Q-12      Q-13     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-12      Q-14     H       CH.sub.3 CH.sub.3                                   Q-12      Q-15     H       CH.sub.3 OCH.sub.3                                  Q-12      Q-16     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-12      Q-17     H       Cl.sup.b OCH.sub.3                                  Q-12      Q-18     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-12      Q-19     H       CH.sub.3 CH.sub.3                                   Q-12      Q-20     H       CH.sub.3 OCH.sub.3                                  Q-13      Q-13     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-13      Q-14     H       Cl.sup.b OCH.sub.3                                  Q-13      Q-15     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-13      Q-16     H       CH.sub.3 CH.sub.3                                   Q-13      Q-17     H       CH.sub.3 OCH.sub.3                                  Q-13      Q-18     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-13      Q-19     H       Cl.sup.b OCH.sub.3                                  Q-13      Q-20     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-14      Q-14     H       CH.sub.3 CH.sub.3                                   Q-14      Q-15     H       CH.sub.3 OCH.sub.3                                  Q-14      Q-16     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-14      Q-17     H       Cl.sup.b OCH.sub.3                                  Q-14      Q-18     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-14      Q-19     H       CH.sub.3 CH.sub.3                                   Q-14      Q-20     H       CH.sub.3 OCH.sub.3                                  Q-15      Q-15     H       CH.sub.3 OCH.sub.3                                  Q-15      Q-16     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-15      Q-17     H       Cl.sup.b OCH.sub.3                                  Q-15      Q-18     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-15      Q-19     H       CH.sub.3 CH.sub.3                                   Q-15      Q-20     H       CH.sub.3 OCH.sub.3                                  Q-16      Q-16     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-16      Q-17     H       Cl.sup.b OCH.sub.3                                  Q-16      Q-18     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-16      Q-19     H       CH.sub.3 CH.sub.3                                   Q-16      Q-20     H       CH.sub.3 OCH.sub.3                                  Q-17      Q-17     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-17      Q-18     H       Cl.sup.b OCH.sub.3                                  Q-17      Q-19     H       OCF.sub.2 H                                                                             OCH.sub.3                                  Q-17      Q-20     H       CH.sub.3 CH.sub.3                                   Q-18      Q-18     H       CH.sub.3 OCH.sub.3                                  Q-18      Q-19     H       OCH.sub.3                                                                               OCH.sub.3                                  Q-18      Q-20     H       Cl.sup.b OCH.sub.3                                  Q-19      Q-19     H       CH.sub.3 CH.sub.3                                   Q-19      Q-20     H       CH.sub.3 OCH.sub.3                                  Q-20      Q-20     H       OCH.sub.3                                                                               OCH.sub.3                                  ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE 16                                                         ______________________________________                                                           Weight Percent*                                                          Active                                                                         Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions.                                                                              3-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9  0-15                                         High Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                          *Active ingredient plus at least one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 10 Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                            80%                                               3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide                                   sodium alkylnaphthalenesulfonate                                                                            2%                                                sodium ligninsulfonate       2%                                                synthetic amorphous silica   3%                                                kaolinite                    13%                                               ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

EXAMPLE 11 Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                       50%                                               2,6-bis(methylthio)benzenesulfonamide                                          sodium alkylnaphthalenesulfonate                                                                            2%                                                low viscosity methyl cellulose                                                                              2%                                                diatomaceous earth           46%                                               ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 12 Granule

    ______________________________________                                         Wettable Powder of Example 11                                                                            5%                                                   attapulgite granules      95%                                                  (U.S.S. 20-40 mesh: 0.84-0.42 mm)                                              ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 13 Extruded Pellet

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                            25%                                               3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide                                   anhydrous sodium sulfate     10%                                               crude calcium ligninsulfonate                                                                               5%                                                sodium alkylnaphthalenesulfonate                                                                            1%                                                calcium/magnesium bentonite  59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 14 Low Strength Granule

    ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                       19%                                               2,6-bis(methylthio)benzenesulfonamide                                          N,N--dimethylformamide       9%                                                attapulgite granules         90%                                               (U.S.S. 20-40 sieve)                                                           ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 15 Aqueous Suspension

    ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                       40%                                               2,6-bis(methylthio)benzenesulfonamide                                          polyacrylic acid thickener   0.3%                                              dodecylphenol polyethylene glycol ether                                                                     0.5%                                              disodium phosphate           1%                                                monosodium phosphate         0.5%                                              polyvinyl alcohol            1.0%                                              water                        56.7%                                             ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 16 Solution

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                            5%                                                3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide.                                  sodium salt                                                                    water                        95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 17 Low Strength Granule

    ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                       0.1%                                              2,6-bis(methylthio)benzenesulfonamide                                          attapulgite granules         99.9%                                             (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 18 Granule

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                            80%                                               3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide                                   wetting agent                1%                                                crude ligninsulfonate salt (containing                                                                      10%                                               5-20% of the natural sugars)                                                   attapulgite clay             9%                                                ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 19 High Strength Concentrate

    ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                       99%                                               2,6-bis(methylthio)benzenesulfonamide                                          silica aerogel               0.5%                                              synthetic amorphous silica   0.5%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 20 Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                            90%                                               3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide                                   dioctyl sodium sulfosuccinate                                                                               0.1%                                              synthetic fine silica        9.9%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 micons. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 21 Wettable Powder

    ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                       40%                                               2,6-bis(methylthio)benzenesulfonamide                                          sodium ligninsulfonate       20%                                               montmorillonite clay         40%                                               ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 22 Oil Suspension

    ______________________________________                                         N--[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-                                                       35%                                               2,6-bis(methylthio)benzenesulfonamide                                          blend of polyalcohol carboxylic                                                                             6%                                                esters and oil soluble petroleum                                               sulfonates                                                                     xylene                       59%                                               ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

EXAMPLE 23 Dust

    ______________________________________                                         N--[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                            10%                                               3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide                                   attapulgite                  10%                                               Pyrophyllite                 80%                                               ______________________________________                                    

The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

Utility

Test results indicate that the compounds of the present invention are active herbicides. They should have utility for broad-spectrum pre and/or postemergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Alternatively, many of the subject compounds should be useful for the selective pre or postemergence weed control in crops, especially wheat and sugar beets.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as selective or general herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.005 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, or for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any other commercial herbicide, examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.

The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

Test A

Speeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, sugar beet, rice, wheat and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species, along with cotton and bush bean, were treated with a soil/foilage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:

C=chlorosis/necrosis;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

U=unusual pigmentation; and

6Y=abscised buds or flowers. ##STR120##

                  TABLE A                                                          ______________________________________                                                   Cmpd. 1  Compound 2      Cmpd. 3                                     Rate g/ha 50       50        400     50                                        ______________________________________                                         POST-                                                                          EMERGENCE                                                                      Bush bean 3C,3H    5C,9G,6Y  6C,9G,6Y                                                                               4C,8H,6Y                                  Cotton    4C,8G    4C,9G     4C,9G   4C,9G                                     Morningglory                                                                             9C       4C,9G     5C,9G   5C,9G                                     Cocklebur 9C       9C        9C      5C,9G                                     Sicklepod 4C,3H    2C,2H     2C,6G   4C,9G                                     Nutsedge  4C,9G    8G        4C,9G   4C,9G                                     Crabgrass 4G       2C,5G     2C,8G   2C,5G                                     Barnyardgrass                                                                            4C,9H    2C,7H     5C,9G   3C,9H                                     Wild Oats 3C,5G    2C,4G     4C,9G   2C                                        Wheat     5G       3G        9G      3G                                        Corn      2C,6H    2C,9H     1U,9G   2C,8H                                     Soybean   5C,9G    5C,9G     5C,9G   5C,9G                                     Rice      2C,7G    2C,4G     2C,8G   1C,1H                                     Sorghum   3C,8H    3C,9G     5C,9G   2C,9G                                     Sugar beet                                                                               2C,8G    2C        4C,8G   2C,8G                                     PRE-                                                                           EMERGENCE                                                                      Morningglory                                                                             2C,9G    2C,8H     9C      4C,9G                                     Cocklebur 9H       9H        9H      9H                                        Sicklepod 3C,6G    2C,2G     2C,9G   4C,5H                                     Nutsedge  2C,6G    5G        10E     4C,6G                                     Crabgrass 2G       2G        7G      2G                                        Barnyardgrass                                                                            5C,6G    3C,7G     5C,9H   5C,6G                                     Wild Oats 2C,8G    3C,8G     5C,9H   3C                                        Wheat     8G       2C,8G     3C,9H   1C,4G                                     Corn      2C,8H    2C,9H     4C,9H   9G                                        Soybean   4C,5G    4C,6H     9H      5C,6H                                     Rice      4C,6G    4C,6G     4C,9H   3C,3G                                     Sorghum   4C,9H    3C,9H     10H     5C,9G                                     Sugar beet                                                                               3C,9G    2C,9G     9G      8G                                        ______________________________________                                                  Cmpd. 4   Cmpd. 5   Cmpd. 6 Cmpd. 7                                   Rate g/ha                                                                               50        50        50      50                                        ______________________________________                                         POST-                                                                          EMER-                                                                          GENCE                                                                          Bush bean                                                                               4C,9G,6Y  2C,7G,6Y  4C,8H,6Y                                                                               3C,8G 6Y                                  Cotton   5C,9G     4C,9G     5C,9H   2C,2H,5G                                  Morningglory                                                                            5C,9G     4C,9G     4C,7G   2C                                        Cocklebur                                                                               9C        9C        9C      3C,8H                                     Sicklepod                                                                               9C        5C,9G     5C,9G   2C,5G                                     Nutsedge 9C        2C,9G     5C,9G   1C,5G                                     Crabgrass                                                                               2C,9G     2C,8G     2C,8G   5G                                        Barnyardgrass                                                                           9C        9C        9C      3C,9H                                     Wild Oats                                                                               9C        9C        5C,9G   5G,2C                                     Wheat    9C        10C       9C      1C,3G                                     Corn     9C        3U,9G     2C,9H   2C,9H                                     Soybean  4C,9G     5C,9G     5C,9G   3C,7G                                     Rice     5C,9G     5C,9G     5C,9G   4C,9G                                     Sorghum  5U,9G     5C,9G     4C,9G   3C,9G                                     Sugar beet                                                                              9C        9C        9C      2C,8G                                     PREEMER-                                                                       GENCE                                                                          Morningglory                                                                            9C        9C        9G      8G                                        Cocklebur                                                                               9H        9H        9H      --                                        Sicklepod                                                                               9C        4C,9G     9G      9G                                        Nutsedge 10E       10E       10E     0                                         Crabgrass                                                                               4C,9G     3C,5G     1C      2G                                        Barnyardgrass                                                                           5C,9H     5C,9H     5C,9H   2C,8H                                     Wild Oats                                                                               5C,9G     5C,9H     5C,9G   2C,8G                                     Wheat    10C       10H       4C,9H   7G                                        Corn     10E       9H        3C,9H   2C,8G                                     Soybean  9H        8H        9H      1C,3G                                     Rice     10E       10E       10E     2C,9H                                     Sorghum  5C,9H     10H       5C,9H   5C,9H                                     Sugar beet                                                                              10C       9C        5C,9G   5C,9G                                     ______________________________________                                                           Cmpd. 8   Cmpd. 9                                            Rate g/ha         50        50                                                 ______________________________________                                         POSTEMERGENCE                                                                  Bush bean         5C,9G,6Y  2H                                                 Cotton            4C,9G     2C                                                 Morningglory      2C,4G     1C                                                 Cocklebur         3C,9H     2C,5G                                              Sicklepod         4C,9G     5G                                                 Nutsedge          4G        2G                                                 Crabgrass         2C,5G     5G                                                 Barnyardgrass     2C,8H     2C,3G                                              Wild Oats         2C,8H     0                                                  Wheat             6C,9G     0                                                  Corn              4C,9H     2C,3G                                              Soybean           3C,9G     2C,5G                                              Rice              5C,9G     2C                                                 Sorghum           2C,9G     9H                                                 Sugar beet        3C,9G     2C,8G                                              PREEMERGENCE                                                                   Morningglory      8G        7G                                                 Cocklebur         9H        8H                                                 Sicklepod         7G        6G                                                 Nutsedge          10E       10E                                                Crabgrass         0         2G                                                 Barnyardgrass     2C,5G     2C,7G                                              Wild Oats         2C,7G     2C,7G                                              Wheat             2C,7G     9G                                                 Corn              2C,7G     2C,5G                                              Soybean           1C,1H     1C,1H                                              Rice              3C,9H     3C,9H                                              Sorghum           2C,9H     5C,9H                                              Sugar beet        3C,9G     3C,9G                                              ______________________________________                                                      Cmpd. 10 Cmpd. 11 Cmpd. 12                                                                              Cmpd. 13                                 Rate g/ha    50       50       50     50                                       ______________________________________                                         POSTEMERGENCE                                                                  Cotton       5C,9G    5C,9G    2C,8H  2C,8G                                    Morningglory 10C      10C      3C,9G  3C,8G                                    Cocklebur    9C       9C       5C,9G  3C,9G                                    Sicklepod    4C,8G    4C,7G    3C     2C                                       Nutsedge     6C,9G    4C,9G    2C,8G  3C,9G                                    Crabgrass    5C,8G    0        2G     0                                        Barnyardgrass                                                                               10C      9C       3C,8H  3C,8H                                    Wild Oats    9C       9C       5G     0                                        Wheat        9C       3C,9G    0      2G                                       Corn         3C,9G    2U,9G    0      0                                        Soybean      3C,9G    4C,9G    2C,9G  2C,9G                                    Rice         3G       4C,9G    5G     4G                                       Sorghum      10C      9C       2C,8G  2C,9G                                    Sugar beet   10C      10C      5G     5G                                       PREEMERGENCE                                                                   Morningglory 9G       9H       2C,7H  9C                                       Cocklebur    9H       9H       9H     9H                                       Sicklepod    5C,8G    6G,5C    2C,7G  8G                                       Nutsedge     2C,5G    0        5G     2C,9G                                    Crabgrass    1C       0        0      0                                        Barnyardgrass                                                                               1C       2C       2C,6H  3C,8H                                    Wild Oats    3C,9G    5C,9G    2C,9G  2C,8G                                    Wheat        2C,4G    8G       2G     2C,7G                                    Corn         3C,9G    9G       5G     2C,8G                                    Soybean      3C,7H    3C,8H    2C,3H  3C,7H                                    Rice         3C,4G    5G       2C,6G  2C,6G                                    Sorghum      5C,9H    6C,9H    2C,9H  2C,9H                                    Sugar beet   9C       10C      8G     2C,9G                                    ______________________________________                                                           Cmpd. 14 Cmpd. 15                                            Rate g/ha         50       50                                                  ______________________________________                                         POSTEMERGENCE                                                                  Cotton            2C,8G    2C,8G                                               Morningglory      2C,5G    4C,9G                                               Cocklebur         2C,7H    5C,9G                                               Sicklepod         2C,3G    3C,6H                                               Nutsedge          10C      3C,9G                                               Crabgrass         3H       0                                                   Barnyardgrass     2C,8H    9C                                                  Wild Oats         0        9C                                                  Wheat             0        9C                                                  Corn              1H       3H                                                  Soybean           2C,9G    3C,9G                                               Rice              5G       2C,9G                                               Sorghum           2C,8H    3C,9G                                               Sugar beet        3G       3C,9G                                               PREEMERGENCE                                                                   Morningglory      9G       9C                                                  Cocklebur         9H       9H                                                  Sicklepod         7G       3C,7G                                               Nutsedge          5G       0                                                   Crabgrass         0        0                                                   Barnyardgrass     2C,7G    4G                                                  Wild Oats         2C       2C,8G                                               Wheat             3G       3G                                                  Corn              2C,7H    2C,9H                                               Soybean           1C,1H    3C,5H                                               Rice              3C,6G    7G                                                  Sorghum           3C,7H    2C,9G                                               Sugar beet        7G       9G                                                  ______________________________________                                    

To better define the utility of the compounds of this invention, several of the compounds were tested in Tests B-F.

Test B

Two plastic bulb pans were filled with fertilized and limed Woodstown sandy loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grass weeds. The other pan was planted with cotton, soybeans, rapeseed, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grass and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), cocklebur (Xanthium pensylvanicum), morningglory (Ipomoea hederacea), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa), velvetleaft (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugar beets. The above four containers were treated preemergence with several test compounds within the scope of the invention.

Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. Compounds 1-6 each exhibited a broad-spectrum of control at application rates as low as 16 g/ha; Compounds 1, 2 and 3 were also safe on wheat at application rates as high as 125 g/ha. Compounds 7-9 showed some activity at 16 g/ha, but exhibited a broader spectrum of activity at rates of 62 g/ha and above. Compounds 7 and 8 also showed some safety on wheat. The data for several of the compounds tested are summarized in Table B.

                  TABLE B                                                          ______________________________________                                         PREEMERGENCE ON                                                                WOODSTOWN SANDY LOAM                                                           ______________________________________                                                     Compound 1  Compound 2                                             Rate g/ha     16      25        16    125                                      ______________________________________                                         Crabgrass     0       0         0     2G                                       Barnyardgrass 3G      9G        2G    9G                                       Sorghum       9G      9G        7G    9G                                       Wild Oats     2G      8G        2G    7G                                       Johnsongrass  3G      9G        5G    9G                                       Dallisgrass   0       6G        3G    3G                                       Giant foxtail 3G      4G        4G    3G                                       Ky. bluegrass --      --        --    --                                       Cheatgrass    6G      8G        7G    9G                                       Sugar beets   5G      10C       5G    8G                                       Corn          2G      5G,3C     3G    9G                                       Rape          9G      10C       9G    9G                                       Cocklebur     6G      9G        7G    9G                                       Nutsedge      7G      10C       4G    10C                                      Cotton        9G      8G        8G    6G                                       Morningglory  6G      9G        3G    7G                                       Sicklepod     5G      7G        2G    6G                                       Teaweed       5G      8G        2G    6G                                       Velvetleaf    5G      8G        0     8G                                       Jimsonweed    3G      9G        0     8G                                       Soybean       2G      8G,7H     0     6G,3H                                    Rice          8G      9G        7G    3G                                       Wheat         0       2G        0     0                                        ______________________________________                                                   Compound 5  Compound 7                                               Rate g/ha   β   62       4    16   62  250                                ______________________________________                                         Crabgrass   2G       7G       0    0    0   0                                  Barnyardgrass                                                                              5G       9G       0    0    0   7G                                 Sorghum     9G       9G       --   --   --  --                                 Wild Oats   6G       9G       0    0    0   5G                                 Johnsongrass                                                                               8G       9G       0    0    0   7G                                 Dallisgrass 3G       8G       --   --   --  --                                 Giant foxtail                                                                              3G       8G       0    0    0   2G                                 Ky. bluegrass                                                                              3G       9G       --   --   --  --                                 Cheatgrass  9G       10C      --   --   --  --                                 Sugar beets 6G       9G       0    3G   7G  9G                                 Corn        3G,2C    4G,2C    0    0    4G  8G                                 Rape        5G       9G       --   --   --  --                                 Cocklebur   5G       9G       0    0    7G  9G                                 Nutsedge    3G       8G       0    0    3G  8G                                 Cotton      5G       7G       0    0    3G  7G                                 Morningglory                                                                               0        8G       0    0    0   5G                                 Sicklepod   0        8G       0    0    4G  9G                                 Teaweed     3G       8G       0    0    3G  7G                                 Velvetleaf  5G       8G       0    0    2G  9G                                 Jimsonweed  7G       9G       0    0    3G  2G                                 Soybean     3G       8G,7H    0    0    2G  7G                                 Rice        8G       10C      0    3G   8G  10G                                Wheat       2G       7G       0    0    0   5G                                 ______________________________________                                    

Test C

The test chemicals, dissolved in a non-phytotoxic solvent, were applied in an overall spray to the foliage and surrounding soil of selected plant species. Approximately fourteen days after treatment, all species were visually compared to untreated controls and rated for response to treatment. The rating system was as described previously for Test A. The data are presented in Table C.

All plant species were seeded in Woodstown sandy loam soil and grown in a greenhouse. The following species were grown in soil contained in plastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), Sicklepod (Cassia obtusifolia), morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria sp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crustgalli), glant foxtail (Setaria faberil) and wild oats (Avena fatua). The following species were grown in soil in a paper cup (12 cm diameter by 13 cm deep): sunflower, sugar beets, and mustard. All plants were sprayed approximately 14 days after planting. Additional plant species such as johnsongrass and field bindweed are sometimes added to this standard test.

Compounds 1-5 were tested by this procedure, and each exhibited postemergence activity at application rates as low as 4 g/ha. Compounds 2 and 3 were safe on wheat, and Compound 3 was also safe on sugar beets. Data for these compounds are presented in Table C.

                  TABLE C                                                          ______________________________________                                         Over-the-Top Soil/Foliage Treatment                                            ______________________________________                                                    Cmpd. 1  Cmpd. 2    Cmpd. 3                                         Rate g/ha    4      16      4    16    4    16                                 ______________________________________                                         Soybeans     7G     8G      3C   8C    8C   9C                                 Velvetleaf   3G     6G      5G   7G    4G   6G                                 Sesbania     5G     8G      4G   7G    8G   8G                                 Sicklepod    0      5G      0    0     2C   6C                                 Cotton       0      5G      5G   6G    4G   5G                                 Morningglory 7G     9G      6G   8G    2G   8G                                 Bush Bean    --     --      --   --    --   --                                 Jimsonweed   8G     9G      5G   5G    0    --                                 Cocklebur    3G     8G      6G   8G    7G   7G                                 Sunflower    --     --      --   --    --   --                                 Mustard      --     --      --   --    --   --                                 Sugar beets  6G     6G      2G   6G    0    0                                  Corn         0      2G      2G   4G    0    4H                                 Crabgrass    0      0       0    0     0    0                                  Rice         0      0       0    0     2G   0                                  Nutsedge     0      0       0    0     2C   8G                                 Barnyardgrass                                                                               0      7G      2G   0     4G   5G                                 Wheat        0      3G      0    0     0    0                                  Giant foxtail                                                                               0      2G      0    0     0    0                                  Wild Oats    0      2G      0    0     0    0                                  Sorghum      --     --      --   --    --   --                                 Johnsongrass 0      3G      1G   3G    4G   7G                                 Field Bindweed                                                                              --     --      --   --    --   --                                 ______________________________________                                                     Compound 4                                                         Rate g/ha     1      4        16      62                                       ______________________________________                                         Soybeans      8G     10C      10C     10C                                      Velvetleaf    2C     6C       7C,7G   7C,8G                                    Sesbania      --     4G       9G      9C                                       Sicklepod     2C     0        9G      9G                                       Cotton        5G     4C       9G      10C                                      Morningglory  5G     8G       8C,8G   9G                                       Bush Bean     --     --       7C,7G   8C,8G                                    Jimsonweed    0      0        9G      9G                                       Cocklebur     2G     --       8G      9G                                       Sunflower     --     --       9C      10C                                      Mustard       --     --       8G      9G                                       Sugar beets   3G     7G       9G      10C                                      Corn          3G     5G       7G      7G                                       Crabgrass     0      0        8G      8G                                       Rice          1C     5C       7G      7G                                       Nutsedge      2G     3G       6G      8C                                       Barnyardgrass 2G     9G       8G      9C                                       Wheat         0      5G       6G      8G                                       Giant foxtail 0      4G       7G      9G                                       Wild Oats     0      4G       7G      8G                                       Sorghum       0      5G       8G      9C                                       Johnsongrass  3G     9C       10C     10C                                      Field Bindweed                                                                               0      6C       3G      5G                                       ______________________________________                                                      Compound 5                                                        Rate g/ha      4         16        62                                          ______________________________________                                         Soybeans       7G        10C       10C                                         Velvetleaf     5C,5G     7C,7G     6C,7G                                       Sesbania       8G        9G        9G                                          Sicklepod      4G        8G        9G                                          Cotton         7G        9G        10C                                         Morningglory   7G        8G        10C                                         Bush Bean      4G,4C     10C       10C                                         Jimsonweed     5G        7G        8G                                          Cocklebur      8G        8G        9G                                          Sunflower      5G        8G        10C                                         Mustard        7G        10C       10C                                         Sugar beets    8G        10C       10C                                         Corn           1G        6G        6G,6C                                       Crabgrass      0         1G        3G                                          Rice           2G        7G,4C     5C,7G                                       Nutsedge       1G        5G        8G                                          Barnyardgrass  7G        8G        8G,6C                                       Wheat          4G        4G        5G                                          Giant foxtail  2G        5G        8G                                          Wild Oats      5G        7G        7G                                          Sorghum        8G        9G        9G                                          Johnsongrass   4G        7G        7C,8G                                       Field Bindweed 1G        0         0                                           ______________________________________                                    

Test D

Two plastic pans lined with polyethylene liners were filled with prepared Woodstown sandy loam soil. One pan was planted with seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), wild oats (Avena fatua), cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis), Italian ryegrass (Lolium multiflorum) and rapeseed (Brassica napus). The other pan was planted with seeds of Russian thistle (Salsola kali), cleavers (Galium aparine), speedwell (Veronica persica), kochia (Kochia scoparia), shepherdspurse (Capsella bursa-pastoris), Matricaria inodora, black nightshade (Solanum nigrum), wild buckwheat (Polygonum convolvulus) and sugar beets (Beta vulgaris). The above two pans were treated preemergence. At the same time two pans in which the above plant species were growing were treated postemergence. Plant heights at the time of treatment ranged from 1-20 cm depending on plant species.

The compounds applied were diluted with a nonphytotoxic solvent and sprayed over-the-top of the pans. An untreated control and a solvent alone control were included for comparison. All treatments were maintained in the greenhouse for 19-22 days at which time the treatments were compared to the controls and the effects visually rated. The recorded data are presented in Table D. Each of the tested compounds provides control of certain weeds at rates of application which cause no, or minimum injury to sugar beets.

                  TABLE D                                                          ______________________________________                                                     Compound 1                                                                     Preemergence                                                                              Postemergence                                           Rate g/ha     15      60       15     60                                       ______________________________________                                         wheat         0       2G       0      0                                        barley        2G      7G       0      0                                        wild oats     3G      6G       0      1G                                       cheatgrass    3G      6G       0      1G                                       blackgrass    9G      9G       0      1G                                       annual bluegrass                                                                             4G      7G       0      0                                        green foxtail 2G      3G       0      0                                        Italian ryegrass                                                                             2G      3G       0      0                                        rapeseed      7G      8G       3G     8G                                       Matricaria inodora                                                                           6G      9G       6G,2C  8G,3C                                    Galium aparine                                                                               10C     10C      10C    10C                                      Russian thistle                                                                              4G      10C      0      0                                        shepherdspurse                                                                               4G      10C      7G     9G                                       kochia        0       0        0      0                                        black nightshade                                                                             2G      8G,3C    6G     8G,7C                                    speedwell     0       6G       2G     8G                                       wild buckwheat                                                                               0       6G       2G,1C  8G,8C                                    sugar beets   0       0        0      0                                        ______________________________________                                                     Compound 2                                                                     Preemergence                                                                              Postemergence                                           Rate g/ha     15      60       15     60                                       ______________________________________                                         wheat         0       0        0      2G                                       barley        0       3G       0      3G                                       wild oats     0       4G       0      3G                                       cheatgrass    1C      1G,4C    0      2G                                       blackgrass    0       4G       0      3G                                       annual bluegrass                                                                             0       0        0      1G                                       green foxtail 0       0        0      0                                        Italian ryegrass                                                                             0       0        0      0                                        rapeseed      1C      10C      10C    8G,1C                                    Matricaria inodora                                                                           8G      8G       3G     6G,4C                                    Galium aparine                                                                               10C     10C      --     10C                                      Russian thistle                                                                              0       0        0      1G                                       shepherdspurse                                                                               8G      10C      7G     9G                                       kochia        0       6G       0      4G                                       black nightshade                                                                             7G      9G,9C    3G,2C  8G,8C                                    speedwell     6G      8G,3C    2C,4G  8G,7C                                    wild buckwheat                                                                               0       5G       2C     7G,4C                                    sugar beets   0       6G       0      0                                        ______________________________________                                                     Compound 3                                                                     Preemergence                                                                              Postemergence                                           Rate g/ha     15      60       15     60                                       ______________________________________                                         wheat         1G      2G,1C    0      0                                        barley        1G      1C       0      1G                                       wild oats     1G,2C   3G       0      0                                        cheatgrass    0       0        0      0                                        blackgrass    6G      7G       0      3G                                       annual bluegrass                                                                             2G      2G       0      2G                                       green foxtail 0       3G       0      0                                        Italian ryegrass                                                                             2G      5G       0      0                                        rapeseed      8G      10C      9G,9C  10C                                      Matricaria inodora                                                                           9G      9G       5G,2C  9G,7C                                    Galium aparine                                                                               --      10C      --     10C                                      Russian thistle                                                                              0       0        5G     7G                                       shepherdspurse                                                                               10C     10C      10C    10C                                      kochia        2G      2G       0      1G                                       black nightshade                                                                             3G      4G       3G,4C  7G,3C                                    speedwell     2G      7G       8G,7C  9G,2C                                    wild buckwheat                                                                               5G      6G       9G,5C  8G,3C                                    sugar beets   0       2G,1C    0      0                                        ______________________________________                                    

Test E

Compounds 2 and 3 were further evaluated for their utility as selective sugar beet herbicides in a test which differed from Test D only in the types of certain weed species. The compounds were applied both pre and postemergence to the species shown in Table E. The relative tolerance of sugar beets is again evident from the data presented in Table E.

                  TABLE E                                                          ______________________________________                                                  Compound 2      Compound 3                                                     Preemergence                                                          Rate g/ha  4        15      60     30    125                                   ______________________________________                                         wheat      0        1G      2G     0     2G                                    barley     0        1G      2G     0     4G                                    wild oats  0        1G      2G     0     0                                     ryegrass   0        2G      1G     0     2G                                    annual bluegrass                                                                          0        0       4G     0     3G                                    blackgrass 0        0       5G     0     1G                                    green foxtail                                                                             0        0       0      0     0                                     Matricaria inodora                                                                        9G       8G      9G     9G,7C 9G,7C                                 Galium aparine                                                                            0        4G,3C   10C    0     0                                     kochia     0        3G      8G     0     1C                                    black nightshade                                                                          8G       9G      9G,7C  2G,1C 7G                                    speedwell  0        2C      8G,8C  6G,5C 8G                                    wild buckwheat                                                                            2G       4G,3C   8G,8C  4G,2C 8G,3C                                 wild mustard                                                                              7G,1C    9G,9C   9G,9C  7G,2C 9G,9C                                 wild radish                                                                               1G,1C    9G      10C    7G,4C 9G,9C                                 sugar beets                                                                               3G       7G      8G     2G,1C 8G                                    ______________________________________                                                  Compound 2      Compound 3                                                     Postemergence                                                         Rate g/ha  4        15      60     30    125                                   ______________________________________                                         wheat      0        0       4G     0     0                                     barley     0        0       4G     0     2G                                    wild oats  0        0       3G     0     0                                     ryegrass   0        0       2G,4C  0     1G                                    annual bluegrass                                                                          0        0       5G     0     0                                     blackgrass 0        0       5G     0     0                                     green foxtail                                                                             0        1G      2G     0     0                                     Matricaria inodora                                                                        0        2C      2G,4C  8G,8C 9G,9C                                 Galium aparine                                                                            1C       4C      5G,5C  7G    10C                                   kochia     0        0       0      3G    2G                                    black nightshade                                                                          6G,2C    5G,4C   9G,4C  6G    8G,7C                                 speedwell  0        0       4G,5C  8G    9G,4C                                 wild buckwheat                                                                            0        1C      2G,3C  0     7G,5C                                 wild mustard                                                                              4C       7G,6C   8G,7C  9G,7C 10C                                   wild radish                                                                               5G,2C    7G,6C   10C    10C   10C                                   sugar beets                                                                               0        3G      3G,2C  0     2G,3C                                 ______________________________________                                    

Test F

Postemergence

Two round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was plated with blackgrass (Alopecurus myosuroides), sugarbeets, nutsedge (Cyperus rotundus) tubers, crabgrass (Digitaria sanguinalis), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa). jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti), and giant foxtail (Setaria faberii). The other pan was planted with wheat, cotton, rice, corn, soybean, wild oats (Avena fatus), cocklebur (Xanthium pensylvanicum), morningglory (Ipomoea hederacea), johnsongrass (Sorghum halepense) and barnyardgrass (Echinochloa crusgalli). The plants were grown for approximately fourteen days, then sprayed postemergence with the chemicals dissolved in a non-phytotoxic solvent.

Preemergence

Two round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil. One pan was planted with blackgrass (Alopercurus myosuroides), sugarbeets, nutsedge, crabgrass, sicklepod, teaweed, jimsonweed, velvetleaf, and giant foxtail. The other pan was planted with wheat, cotton, rice, corn, soybeans, wild oats, cocklebur, morningglory, johnsongrass, and barnyardgrass. The two pans were sprayed preemergence with the chemicals dissolved in a non-phytotoxic solvent.

Treated plants and controls were maintained in the greenhouse for 28 days, then all treated plants were compared to controls and visually rated for plant response utilizing the rating system peviously described for Test A.

Response ratings are contained in Table F.

                  TABLE F                                                          ______________________________________                                         Compound 10                                                                                Postemergence                                                      Rate g/ha     1       4        16     62                                       ______________________________________                                         corn          0       3G       8G     9G                                       wheat         0       0        0      0                                        rice          0       0        0      2G                                       soybean       4G      7G       9G     9G                                       cotton        0       2C       7G     8G                                       sugarbeet     0       5G       10C    10C                                      crabgrass     0       0        0      3G                                       johnsongrass  0       3G       8G     10G                                      blackgrass    0       0        5G     9G                                       barnyardgrass 0       4G       7G     10C                                      nutsedge      0       0        3G     8G                                       giant foxtail 0       0        2G     4G                                       wild oats     0       0        3G     5C                                       cocklebur     3G      9G       9G     9G                                       morningglory  2G      6G       7G     9G                                       teaweed       0       0        0      2G                                       sicklepod     0       0        3G     3G                                       jimsonweed    0       4G       8G     10G                                      velvetleaf    0       3G       6G     5G                                       ______________________________________                                         Compound 10                                                                                Preemergence                                                       Rate g/ha     4       16       62     250                                      ______________________________________                                         corn          0       0        2G     8G                                       wheat         0       0        2G     8G                                       rice          0       2G       5G     10B                                      soybean       2C      4H       8G     9G                                       cotton        0       0        2G     6C                                       sugarbeet     2G      5G       10E    10B                                      crabgrass     0       0        2G     9G                                       johnsongrass  2G      4G       8G     9B                                       blackgrass    2G      4G       8E     10E                                      barnyardgrass 0       2C       7G     9G                                       nutsedge      0       3G       7G     10E                                      giant foxtail 0       0        6G     10E                                      wild oats     0       0        3G     9G                                       cocklebur     2G      6G       9G     9G                                       morningglory  0       2C       6G     9G                                       teaweed       0       0        2C     8G                                       sicklepod     0       0        2C     7G                                       jimsonweed    0       0        3G     8G                                       velvetleaf    0       2C       5C     9G                                       ______________________________________                                         Compound 11                                                                                Postemergence                                                      Rate g/ha     1       4        16     62                                       ______________________________________                                         corn          0       2G       8G     10G                                      wheat         0       0        3G     6G                                       rice          0       0        2G     3C                                       soybean       3G      6G       9G     10G                                      cotton        0       2G       8G     9G                                       sugarbeet     0       5G       9G     10G                                      crabgrass     0       0        3G     5G                                       johnsongrass  0       3G       8C     10C                                      blackgrass    0       4G       8G     10C                                      barnyardgrass 0       4G       6G     10C                                      nutsedge      0       0        5G     9C                                       giant foxtail 0       0        0      5G                                       wild oats     0       0        4G     9C                                       cocklebur     3G      5G       8G     9G                                       morningglory  0       3G       8G     9G                                       teaweed       0       0        0      3G                                       sicklepod     0       0        2G     5G                                       jimsonweed    0       0        3G     9G                                       velvetleaf    0       0        3G     10C                                      ______________________________________                                         Compound 11                                                                                Preemergence                                                       Rate g/ha     4       16       62     250                                      ______________________________________                                         corn          0       0        2G     7G                                       wheat         0       2G       5G     9G                                       rice          0       2G       9G     9G                                       soybean       0       2C       5G     8G                                       cotton        0       0        0      2C                                       sugarbeet     5G      7G       10B    10E                                      crabgrass     0       2G       4G     7G                                       johnsongrass  2G      4G       6C     9G                                       blackgrass    2G      4G       8E     10E                                      barnyardgrass 0       0        5G     8G                                       nutsedge      0       2G       4G     9G                                       giant foxtail 0       0        6G     7G                                       wild oats     0       2G       5G     8G                                       cocklebur     0       3G       7G     9G                                       morningglory  0       2C       4H     8H                                       teaweed       0       0        3C     5C                                       sicklepod     0       0        4G     5G                                       jimsonweed    0       0        4G     8C                                       velvetleaf    0       0        2C     6G                                       ______________________________________                                         Compound 12                                                                                  Postemergence                                                    Rate g/ha       4        16        62                                          ______________________________________                                         corn            0        0         0                                           wheat           0        0         0                                           rice            0        0         0                                           soybean         2G       7G        10G                                         cotton          0        0         3G                                          sugarbeet       0        4G        8G                                          crabgrass       0        0         0                                           johnsongrass    0        0         0                                           blackgrass      0        0         3G                                          barnyardgrass   0        0         0                                           nutsedge        0        3G        6G                                          giant foxtail   0        0         0                                           wild oats       0        0         0                                           cocklebur       4G       9G        10G                                         morningglory    3G       8G        10G                                         teaweed         0        0         0                                           sicklepod       0        2G        4G                                          jimsonweed      2G       6G        9G                                          velvetleaf      0        0         5G                                          ______________________________________                                         Compound 12                                                                                  Preemergence                                                     Rate g/ha       16        62       250                                         ______________________________________                                         corn            0         0        0                                           wheat           0         0        0                                           rice            0         4G       8G                                          soybean         0         2G       5G                                          cotton          0         0        4G                                          sugarbeet       0         0        4G                                          crabgrass       0         0        0                                           johnsongrass    0         3G       9G                                          blackgrass      3G        5G       8G                                          barnyardgrass   0         2G       6G                                          nutsedge        0         2G       6G                                          giant foxtail   0         2G       8G                                          wild oats       0         0        0                                           cocklebur       0         5G       9G                                          morningglory    0         0        6G                                          teaweed         0         0        5G                                          sicklepod       0         0        5G                                          jimsonweed      0         3G       8G                                          velvetleaf      0         2G       8G                                          ______________________________________                                         Compound 13                                                                                Postemergence                                                      Rate g/ha     4       16       62    250                                       ______________________________________                                         corn          0       0        2G    6G                                        wheat         0       0        0     0                                         rice          0       0        0     2G                                        soybean       2G      5G       8G    9G                                        cotton        0       0        3G    8G                                        sugarbeet     0       0        4G    9G                                        crabgrass     0       0        0     0                                         johnsongrass  0       0        0     3G                                        blackgrass    0       0        3G    8G                                        barnyardgrass 0       0        2G    7G                                        nutsedge      0       4G       7G    9G                                        giant foxtail 0       0        0     2G                                        wild oats     0       0        0     0                                         cocklebur     3G      9G       9G    10G                                       morningglory  0       3G       6G    10G                                       teaweed       0       0        0     3G                                        sicklepod     0       0        0     3G                                        jimsonweed    0       0        4G    10G                                       velvetleaf    0       2G       7G    9G                                        ______________________________________                                         Compound 13                                                                                  Preemergence                                                     Rate g/ha       16       62        250                                         ______________________________________                                         corn            0        0         2G                                          wheat           0        0         2G                                          rice            0        2G        6G                                          soybean         0        3G        6G                                          cotton          0        0         3G                                          sugarbeet       0        5G        7G                                          crabgrass       0        0         0                                           johnsongrass    0        3G        7G                                          blackgrass      3G       7G        9G                                          barnyardgrass   0        7G        10G                                         nutsedge        0        0         2G                                          giant foxtail   0        4G        8G                                          wild oats       0        2G        5G                                          cocklebur       3G       8G        9G                                          morningglory    0        0         3G                                          teaweed         0        3G        7G                                          sicklepod       0        0         6G                                          jimsonweed      4G       8G        9G                                          velvetleaf      2G       7G        8G                                          ______________________________________                                         Compound 14                                                                                Postemergence                                                      Rate g/ha     4       16       62     250                                      ______________________________________                                         corn          0       0        0      0                                        wheat         0       0        0      0                                        rice          0       0        0      0                                        soybean       2G      7G       9G     9G                                       cotton        0       0        4G     8G                                       sugarbeet     0       0        3G     10C                                      crabgrass     0       0        0      0                                        johnsongrass  0       0        0      0                                        blackgrass    0       5G       9C     9C                                       barnyardgrass 0       0        0      6G                                       nutsedge      4G      9C       10C    10C                                      giant foxtail 0       0        0      0                                        wild oats     0       0        0      0                                        cocklebur     0       5G       7G     10G                                      morningglory  0       5G       8G     10G                                      teaweed       0       0        0      3G                                       sicklepod     0       0        0      3G                                       jimsonweed    0       3G       7G     10G                                      velvetleaf    0       4G       7G     10G                                      ______________________________________                                         Compound 14                                                                                    Preemergence                                                   Rate g/ha         62         250                                               ______________________________________                                         corn              0          5G                                                wheat             0          0                                                 rice              3G         7G                                                soybean           0          6G                                                cotton            0          0                                                 sugarbeet         0          2G                                                crabgrass         0          0                                                 johnsongrass      0          0                                                 blackgrass        5G         10G                                               barnyardgrass     4G         9G                                                nutsedge          4G         9G                                                giant foxtail     3G         7G                                                wild oats         0          0                                                 cocklebur         2C         9G                                                morningglory      0          0                                                 teaweed           0          0                                                 sicklepod         0          0                                                 jimsonweed        3G         8G                                                velvetleaf        2G         8G                                                ______________________________________                                         Compound 15                                                                                Postemergence                                                      Rate g/ha     4       16       62     250                                      ______________________________________                                         corn          0       0        3G     6G                                       wheat         0       0        0      4G                                       rice          0       0        4G     10G                                      soybean       2G      6G       9G     10G                                      cotton        0       2G       7G     10G                                      sugarbeet     3G      10C      10C    10C                                      crabgrass     0       0        0      0                                        johnsongrass  0       3G       10C    10C                                      blackgrass    0       5G       10G    10G                                      barnyardgrass 0       4G       10G    10C                                      nutsedge      3G      7C       10C    10C                                      giant foxtail 0       2G       6G     10G                                      wild oats     0       3G       7C     9C                                       cocklebur     8G      9G       10G    10C                                      morningglory  3G      8G       10G    10G                                      teaweed       0       0        0      3G                                       sicklepod     0       5G       7G     10C                                      jimsonweed    4G      9G       10G    10G                                      velvetleaf    0       7C       9G     10C                                      ______________________________________                                         Compound 15                                                                                  Preemergene                                                      Rate g/ha       16       62        250                                         ______________________________________                                         corn            0        4G        9G                                          wheat           0        5G        7G                                          rice            3G       9G        10G                                         soybean         3G       7G        9G                                          cotton          0        2G        7G                                          sugarbeet       2G       8G        10G                                         crabgrass       0        3G        6G                                          johnsongrass    3G       9G        10G                                         blackgrass      3G       7G        10G                                         barnyardgrass   3G       8G        10G                                         nutsedge        0        4G        10E                                         giant foxtail   2G       10G       10E                                         wild oats       0        5G        8G                                          cocklebur       2G       8G        9G                                          morningglory    0        4G        7C                                          teaweed         0        4G        5G                                          sicklepod       0        5G        7G                                          jimsonweed      0        3G        9G                                          velvetleaf      0        4G        9G                                          ______________________________________                                     

What is claimed is:
 1. A compound of the formula: ##STR121## wherein R₁ is S(O)_(n) R₅, NR₆ R₇, CO₂ R₈, SO₂ NR₉ R₁₀, ##STR122## OSO₂ R₁₃, CH₂ OR₁₄ or Q; R₂ is S(O)_(m) R₅, NR₆ R₇, CO₂ R₈, SO₂ NR₉ R₁₀, ##STR123## OSO₂ R₁₃, CH₂ OR₁₄ or Q; R₃ is H, Cl, F, Br, CH₃, OCH₃ or CF₃ ;R₄ is H or CH₃ ; R₅ is C₁ -C₃ alkyl; R₆ and R₇ are independently CH₃ or CH₂ CH₃ ; R₈ is C₁ -C₃ alkyl, CH₂ CH═CH₂, CH₂ CH₂ Cl or CH₂ CH₂ OCH₃ ; R₉ is CH₃ or OCH₃ ; R₁₀ is C₁ -C₃ alkyl; R₁₁ is H, Cl, Br, F, CH₃ or OCH₃ ; R₁₂ is H or CH₃ ; R₁₃ is C₁ -C₃ alkyl or CF₃ ; R₁₄ is C₁ -C₃ alkyl or CF₂ H; n is 0, 1 or 2; m is 0 or 1; Q is ##STR124## W is O, S or NR₁₈ ; W' is O or S; R₁₅, R₁₆, R₁₇ and R₁₈ are independently H or CH₃ ; Q is also ##STR125## R₁₉, R₂₀, R₂₂, R₂₄ and R₂₅ are independently H or CH₃ ; R₂₁ and R₂₃ are independently H, CH₃ or OCH₃ ; Q is also ##STR126## R₂₆, R₂₇, R₂₈, R₂₉, R₃₀ and R₃₁ are independently H or CH₃ ; A is ##STR127## Z is CH; X is CH₃, OCH₃, Cl, OCH₂ CH₃, OCF₂ H or F; Y is H, NH₂, NHCH₃, N(CH₃)₂, CH₃, CH₂ CH₃, CF₃, CH₂ OCH₃, CH₂ OCH₂ CH₃, O(C₁ -C₃ alkyl), SCH₃, O(C₃ -C₄ alkenyl), O(C₃ -C₄ alkynyl), OCH₂ CF₃, OCH₂ CH₂ F, OCH₂ CH₂ Cl, OCH₂ CH₂ Br or OCF₂ H;and agriculturally suitable salts thereof; provided that (a) R₁ and R₂ are not simultaneously CO₂ R₈ ; (b) when either one of R₁ or R₂ is SO₂ NR₉ R₁₀, then the other must not be S(O)_(n) R₅, S(O)_(m) R₅, CH₂ OR₁₄ or NR₆ R₇ ; (c) when R₉ is OCH₃, then R₁₀ is CH₃ ; (d) when either one of R₁ or R₂ is CO₂ R₈, then the other must not be S(O)_(n) R₅, S(O)_(m) R₅ or NR₆ R₇ ; (e) the total number of carbon atoms in R₂₆ to R₃₁ combined, is equal to or less than four; (f) when X is Cl or F, then Y is NH₂, NHCH₃, N(CH₃)₂, OCH₃ or OCH₂ CH₃ ; (g) when R₁ is CO₂ R₈ then R₂ is not OSO₂ R₁₃ ; and (h) when X or Y is OCF₂ H, then R₂ is Q.
 2. A compound of claim 1 wherein R₁ and R₂ are not simultaneously Q and R is H.
 3. A compound of claim 2 wherein Y is CH₃, CF₃, CH₂ OCH₃, OCH₃, OCH₂ CF₃ or OCF₂ H.
 4. A compound of claim 3 wherein R₃ is in either the 3- or 5-position.
 5. A compound of claim 4 wherein R₁ and R₂ are not simultaneously SO₂ NR₉ R₁₀ or NR₆ R₇.
 6. A compound of claim 5 wherein R₃ is H and at least one of R₁ or R₂ is S(O)_(n) R₅, S(O)_(m) R₅, CF₃, NR₆ R₇, SO₂ NR₉ R₁₀, ##STR128## OSO₂ R₁₃ or CH₂ OR₁₄.
 7. A compound of claim 6 wherein R₅ is CH₃ or CH₂ CH₃, R₆ and R₇ are both CH₃, R₁₀ is CH₃, R₁₁ is H, R₁₃ is CH₃ or CH₂ CH₃ and R₁₄ is CH₃.
 8. A compound of claim 7 wherein X is CH₃, OCH₃ or Cl and Y is CH₃, OCH₃ or CH₂ OCH₃.
 9. The compound of claim 1 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-methylsulfonyl-1,1'-biphenyl-2-sulfonamide.
 10. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 11. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 12. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
 13. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
 14. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
 15. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
 16. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
 17. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.
 18. An agriculturally suitable composition for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 9 and at least one of the following: surfactant, solid or liquid diluent.
 19. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected postemergence or preemergence an effective amount of a compound of claim
 1. 20. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected postemergence or preemergence an effective amount of a compound of claim
 2. 21. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected postemergence or preemergence an effective amount of a compound of claim
 3. 22. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected postemergence or preemergence an effective amount of a compound of claim
 4. 23. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected postemergence or preemergence an effective amount of a compound of claim
 5. 24. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected postemergence or preemergence an effective amount of a compound of claim
 6. 25. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected postemergence or preemergence an effective amount of a compound of claim
 7. 26. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected postemergence or preemergence an effective amount of a compound of claim
 8. 27. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected postemergence or preemergence an effective amount of a compound of claim
 9. 